1214:. The stomach and small intestine are very important in the absorption of ingested alkaloids. At approximately 2.3 hours after chewing khat leaves, the maximum concentration of cathinone in blood plasma is reached. The mean residence time is 5.2 ± 3.4 hours. The elimination half-life of cathinone is 1.5 ± 0.8 hours. A two-compartment model for absorption and elimination best describes this data. However, at most, only 7% of the ingested cathinone is recovered in the urine. This indicates that the cathinone is being broken down in the body. Cathinone has been shown to selectively metabolize into R,S-(-)-norephedrine and cathine. The reduction of the
1379:
1314:
455:
432:
1391:
47:
1461:
38:
776:
1352:
Aside from the beta- and non-beta-oxidative pathways, the biosynthesis of cathinone can proceed through a CoA-dependent pathway. The CoA-dependent pathway is actually a mix between the two main pathways as it starts like the beta-oxidative pathway and then when it loses CoA, it finishes the synthesis
766:
sample. The researchers analyzed the participants' moods, activity levels and blood pressure before and after consuming the khat or placebo. This analysis showed that cathinone produced amphetamine-like symptoms, leading the researchers to confirm that cathinone, not cathine, is the active ingredient
810:
The cultivation of khat in Yemen is a highly profitable industry for farmers. Khat plants will grow differently depending on the climate they are grown in and each one will produce different amounts of cathinone. It generally grows best in coastal, hot climates. In Yemen, the khat plant is named
1497:
The structure of cathinone is very similar to that of other molecules. By reducing the ketone, it becomes cathine if it retains its stereochemistry, or norephedrine if its stereochemistry is inverted. Cathine is a less potent version of cathinone and cathinone's spontaneous reduction is the reason
1230:
because it led to feelings of happiness and excitement. Chronic khat chewing can also create drug dependence, as shown by animal studies. In such studies, monkeys were trained to push a lever to receive the drug reward. As the monkeys' dependence increased, they pressed the lever at an increasing
1349:. 1-phenylpropane-1,2-dione goes through a transaminase reaction to replace a ketone with an ammonia group to form (S)-cathinone. (S)-Cathinone can then undergo a reduction reaction to produce the less potent but structurally similar cathine or norephedrine, which are also found in the plant.
806:
In order to produce its desired effects, khat leaves should be chewed fresh. The fresh leaves have a higher concentration of cathinone. Waiting too long after cultivation to chew the leaf will allow the cathinone to break down into its less potent form, cathine. Because of the need for quick
745:
was identified as a predominant alkaloid in the plant. Cathine was thought to be the main active ingredient in khat until the 1960s, when it was found that the amount of cathine in the khat leaves is insufficient to produce the effects observed. In 1975, the United
Nations Narcotic Laboratory
1420:
can be brominated, and the bromine can be substituted with ammonia to produce a racemic mixture of cathinone. A different synthetic strategy must be employed to produce enantiomerically pure (S)-cathinone. This synthetic route starts out with the N-acetylation of the
799:, Somalia and Yemen. Men usually chew it during parties or other social gatherings while smoking cigarettes and drinking tea. Farmers and other workers also use khat in the afternoon to reduce fatigue and hunger as the day goes on. It functions like the
758:
and found evidence of a different alkaloid, cathinone. Cathinone is molecularly similar to cathine, but is much more abundant in younger plants. This finding caused scientists to speculate that cathinone was the true active ingredient in khat.
2061:
1201:
Khat leaves are removed from the plant stalk and are kept in a ball in the cheek and chewed. Chewing releases juices from the leaves, which include the alkaloid cathinone. The absorption of cathinone has two phases: one in the
4724:
807:
chewing, it is a habit that has historically been prevalent only where the plant grows. However, in the recent years with improvements in road and air transport, khat chewing has spread to all corners of the world.
1594:
Nutt D, King LA, Blakemore C (March 2007). "Development of a rational scale to assess the harm of drugs of potential misuse". Lancet. 369 (9566): 1047–53. doi:10.1016/S0140-6736(07)60464-4. PMID 17382831. S2CID
1169:
The metabolites of cathinone, cathine and norephedrine, also possess CNS stimulation, but create much weaker effects. The effects of cathinone on the body can be countered by a preceding administration of a
1498:
that older khat plants are not as stimulating as younger ones. Cathinone and amphetamine are closely related in that amphetamine is only lacking the ketone C=O group. Cathinone is structurally related to
114:
1218:
group in cathinone will produce cathine. This reduction is catalyzed by enzymes in the liver. The spontaneous breakdown of cathinone is the reason it must be chewed fresh after cultivation.
1970:
8985:
4478:
2049:
8980:
4769:
4483:
1536:
is one of the most commonly prescribed antidepressants and its structure is
Cathinone with a tertiary butyl group attached to the nitrogen and chlorine attached to the benzene ring
78:
576:
5214:
1094:
Illegal under List I - "Plants and substances with a high risk to the public health due to their harmful effect of misuse, prohibited for use in human and veterinary medicine"
4463:
1234:
Khat chewing and the effects of cathinone on the body differ from person to person, but there is a general pattern of behavior that emerges after ingesting fresh cathinone:
9511:
9521:
3250:
150:
2103:
1532:
There are many cathinone derivatives that include the addition of an R group to the amino end of the molecule. Some of these derivatives have medical uses as well.
1617:
4275:
2009:
4197:
1612:[Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).
163:
2270:
127:
762:
A study was conducted in 1994 to test the effects of cathinone. Six volunteers who had never chewed khat were given an active khat sample and a cathinone-free
1325:
and the first step is carried out by L-phenylalanine ammonia lyase (PAL), which cleaves off an ammonia group and creates a carbon-carbon double bond, forming
532:
2214:"Expressed sequence tag analysis of khat (Catha edulis) provides a putative molecular biochemical basis for the biosynthesis of phenylpropylamino alkaloids"
926:
Legal – The khat plant leaves are allowed to be chewed and beverages containing khat are legal, but it is illegal to sell pills based on cathinone extracts
6835:
9015:
9010:
4508:
4503:
1800:
8063:
8013:
2303:
9030:
9005:
4764:
4498:
4473:
4468:
1226:
The first documentation of the khat plant being used in medicine was in a book published by an
Arabian physician in the 10th century. It was used as an
9025:
9020:
9000:
8995:
7394:
4659:
4493:
1912:
7357:
5207:
9496:
7161:
4408:
1978:
1365:, an intermediate of the non-beta-oxidative pathway. Benzaldehyde is converted into benzoic acid and proceeds through the rest of the synthesis.
4664:
1329:. After this, the molecule can either go through a beta-oxidative pathway or a non-beta-oxidative pathway. The beta-oxidative pathway produces
8033:
7341:
4488:
8558:
2780:
824:
820:
803:
in a strong cup of coffee as an anti-fatigue drug. Students and drivers have been known to use it to stay alert for longer periods of time.
187:
6980:
6272:
5620:
2367:
1529:
leaves over time. Fresh leaves have a greater ratio of cathinone to cathine than dried ones, therefore having more psychoactive effects.
811:
after the region in which it is grown. The Nehmi khat plant has the highest known concentration of cathinone, 342.5 mg/100 g.
9400:
6186:
5498:
5200:
4822:
139:
7930:
6990:
6297:
5640:
4453:
3759:
3665:
2435:
1605:
1748:
Widler P, Mathys K, Brenneisen R, Kalix P, Fisch HU (May 1994). "Pharmacodynamics and pharmacokinetics of khat: a controlled study".
8058:
8048:
8028:
7035:
552:
1939:
8568:
8386:
8053:
8038:
8023:
7806:
6995:
6302:
5645:
3764:
1525:, is a less powerful stimulant. The biophysiological conversion from cathinone to cathine is to blame for the depotentiation of
8681:
8381:
8331:
8043:
7166:
6687:
5932:
4164:
3858:
3769:
828:
226:
99:
1174:. The antagonist prevents synaptic dopamine released by cathinone from exerting its effect by binding to dopamine receptors.
9506:
9121:
8990:
8975:
8970:
8553:
7361:
7131:
6975:
6538:
6507:
6282:
5801:
5775:
5630:
4448:
4418:
3749:
3744:
3444:
3360:
2095:
1841:
Al-Motarreb A, Baker K, Broadley KJ (August 2002). "Khat: pharmacological and medical aspects and its social use in Yemen".
518:
1353:
in the non-beta-oxidative pathway. In this pathway, the trans-cinnamic acid produced from L-phenylalanine is ligated to a
8965:
8960:
8548:
8543:
8308:
7387:
7020:
6970:
6965:
6682:
6277:
5625:
4438:
4423:
3828:
3739:
3734:
3275:
1613:
1609:
2331:
8922:
7925:
7337:
7146:
7136:
7116:
7075:
7050:
7000:
6910:
6517:
6512:
6307:
5785:
5780:
5650:
4443:
4252:
4242:
4101:
4001:
3774:
3556:
2001:
1171:
331:
1378:
9395:
8902:
8897:
7942:
7156:
7151:
7126:
7080:
6790:
6522:
6502:
6126:
6054:
5423:
5353:
4863:
4403:
4290:
4285:
4006:
3245:
1884:
411:
2262:
1313:
1078:
The khat plant itself is allowed to be sold and chewed, but it is illegal to sell or make beverages containing khat
8533:
7411:
7403:
6707:
6657:
4518:
3941:
3863:
3414:
3237:
2179:
9531:
8846:
8676:
7873:
6121:
5418:
5231:
5223:
4571:
3409:
3340:
2755:
832:
175:
7380:
7106:
6905:
6628:
6181:
5901:
5478:
4011:
3848:
2900:
2495:
2360:
1792:
1429:
70:
2295:
1151:
1610:"RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"
8912:
8871:
8595:
8463:
8458:
8448:
8376:
8366:
8120:
8110:
8093:
7952:
7192:
7070:
6885:
6845:
6810:
6800:
6074:
6064:
5373:
5363:
4305:
4300:
3996:
3429:
3370:
3320:
3315:
3265:
2865:
791:
chew khat leaves daily. It is an important piece of the culture and economy in this region, especially in
450:
9072:
9040:
8949:
8588:
8356:
7993:
7902:
7894:
7886:
7878:
7353:
7349:
7217:
7121:
7085:
7060:
6497:
6382:
5770:
5678:
4903:
4779:
4528:
4247:
3936:
3439:
3325:
3285:
3270:
1916:
1565:
1281:
1127:
400:
21:
This article is about the specific chemical compound cathinone. For the class of similar substances, see
8907:
8851:
8724:
8709:
8698:
8351:
8088:
8068:
7212:
7055:
6374:
6332:
5670:
5588:
4744:
4380:
4109:
3931:
2765:
2750:
2742:
1575:
1338:
843:
22:
4842:
1193:
contraction. It can also induce dry mouth, blurred vision and increased blood pressure and heart rate.
1177:
Cathinone can also affect cholinergic concentrations in the gut and airways by blocking prejunctional
9516:
9228:
9087:
9082:
8739:
8729:
8719:
8583:
8371:
8323:
8268:
8258:
8008:
7345:
7065:
7040:
6900:
6855:
6805:
6420:
6364:
6246:
6176:
5891:
5686:
5548:
5473:
5078:
4837:
4589:
3991:
3898:
3868:
3675:
3512:
3290:
2760:
2440:
2430:
2212:
Hagel JM, Krizevski R, Kilpatrick K, Sitrit Y, Marsolais F, Lewinsohn E, Facchini PJ (October 2011).
2125:
Kalix P (1981). "Cathinone, an alkaloid from khat leaves with an amphetamine-like releasing effect".
205:
59:
1440:
forming an acyl chloride. At the same time, a
Friedel-Crafts acylation is preformed on benzene with
9526:
9501:
9390:
9136:
8939:
8886:
8538:
8453:
8443:
8391:
8361:
8297:
8184:
8115:
8105:
7988:
7207:
6945:
6795:
6637:
6415:
6337:
6171:
6069:
6059:
5982:
5916:
5593:
5483:
5368:
5358:
5281:
4594:
4169:
3981:
3812:
3690:
3581:
3517:
3310:
3295:
3255:
2641:
2528:
2353:
1289:
1178:
427:
246:
66:
2340:
8749:
8744:
7846:
7222:
6558:
6553:
6049:
5816:
5348:
4354:
4340:
4295:
4280:
2785:
2770:
2422:
2150:
1866:
1773:
1358:
1317:
Mechanism of the Non-Beta
Oxidation pathway for the biosynthesis of S-Cathinone in the Khat plant
7279:
2031:
7704:
3956:
9077:
8824:
8814:
8784:
8714:
8406:
8149:
7821:
6433:
6257:
6104:
5719:
5553:
5402:
5128:
4513:
4365:
4021:
3389:
3116:
2880:
2820:
2775:
2243:
2142:
1858:
1765:
1715:
1669:
1537:
1491:
1449:
1441:
1285:
1166:
from brain striatal preparations that are prelabelled either with dopamine or its precursors.
1131:
847:
784:
734:
7749:
7744:
7739:
7734:
7724:
7719:
7714:
7709:
7699:
7689:
7679:
7659:
7649:
7644:
7639:
7454:
380:
8819:
8799:
8639:
8303:
8278:
8222:
7862:
7619:
7614:
7564:
7111:
6955:
6865:
6754:
6618:
6492:
6405:
6262:
5998:
5886:
5765:
5709:
5558:
5297:
4649:
4458:
4320:
4202:
3961:
3833:
3823:
3724:
3624:
3459:
3192:
2885:
2533:
2233:
2225:
2134:
1850:
1757:
1705:
1659:
1651:
1422:
1254:
691:
599:
467:
197:
7584:
7474:
7464:
7459:
340:
320:
255:
9415:
9258:
9179:
8426:
8411:
8318:
8293:
8218:
8153:
7998:
7910:
7045:
6890:
6633:
6548:
6438:
6327:
6109:
5972:
5911:
5906:
5811:
5724:
5583:
5407:
5271:
5073:
4566:
4375:
4350:
4310:
4154:
4071:
4026:
3893:
3888:
3808:
3804:
3620:
3393:
3375:
2845:
2543:
2335:
1640:"Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves"
1507:
1437:
1211:
950:
Khat is legal but the cultivation and selling of the plant is regulated by the government
4832:
4827:
4807:
4802:
4797:
4792:
846:
were also often used as the key ingredient of recreational drug mixes commonly known as "
2052:[REGULATION on the procedure for classifying plants and substances as narcotic]
454:
431:
46:
9449:
9330:
9243:
8573:
8194:
7857:
6880:
6643:
6573:
6395:
6292:
6206:
5841:
5699:
5578:
5508:
5068:
5063:
4868:
4330:
4040:
3878:
3586:
2654:
2548:
2503:
2465:
2238:
2213:
1947:
1664:
1639:
1413:
1227:
1155:
1119:
730:
707:
9490:
9465:
9460:
9375:
9284:
9263:
9237:
9195:
9060:
8804:
8659:
8508:
8431:
8169:
7791:
7776:
6613:
6603:
6543:
6466:
6344:
6322:
6131:
5977:
5881:
5871:
5806:
5739:
5600:
5433:
5276:
5148:
5048:
4998:
4913:
4644:
4639:
4159:
4086:
4061:
3976:
3971:
3946:
3911:
3784:
3424:
3365:
2910:
2855:
2694:
2689:
2684:
2679:
2649:
2523:
2445:
1655:
1499:
1483:
1479:
1417:
1326:
1322:
1203:
1190:
1139:
695:
668:
443:
2229:
2154:
1777:
9455:
9370:
9248:
9203:
9151:
9092:
9050:
8789:
8436:
8214:
8209:
8159:
8140:
7816:
7316:
7243:
7187:
7182:
6930:
6830:
6820:
6785:
6588:
6568:
6471:
6216:
6211:
6196:
6116:
6089:
5957:
5952:
5856:
5836:
5744:
5518:
5513:
5493:
5413:
5388:
5256:
5251:
5183:
5103:
5053:
4973:
4953:
4948:
4928:
4923:
4878:
4634:
4629:
4619:
4604:
4543:
4119:
4114:
4091:
4051:
3883:
3789:
3705:
3635:
3616:
3611:
3596:
3469:
3399:
3350:
3028:
2993:
2958:
2825:
2664:
2485:
2470:
1870:
1470:
1390:
1362:
1334:
1265:
1242:
672:
651:
4817:
4812:
1460:
1341:
catalyzed by a ThDP-dependent enzyme (Thiamine diphosphate-dependent enzyme) with
998:
Cathinone and cathine have been illegal but khat was announced as illegal in 2012
280:
9475:
9440:
9410:
9340:
9335:
9310:
9208:
9111:
8764:
8754:
8734:
8688:
8669:
8649:
8628:
8416:
8401:
8336:
8288:
8228:
8199:
8179:
8145:
8073:
7867:
7801:
7311:
7296:
7141:
7025:
6935:
6875:
6583:
6428:
6410:
6226:
6221:
6166:
6161:
6099:
6094:
6033:
6013:
5851:
5714:
5610:
5528:
5523:
5463:
5458:
5398:
5393:
5332:
5312:
5153:
5138:
5123:
5093:
5088:
5033:
5018:
5013:
4988:
4943:
4933:
4918:
4898:
4888:
4883:
4787:
4749:
4395:
4315:
4046:
4016:
3966:
3921:
3838:
3818:
3794:
3630:
3601:
3566:
3489:
3479:
3474:
3449:
3385:
3355:
3227:
3207:
3154:
3096:
3073:
3068:
3058:
3038:
3023:
3018:
3013:
3008:
3003:
2983:
2978:
2943:
2835:
2790:
2709:
2669:
2616:
2513:
2480:
2412:
1913:"Synthetic Street Drug Camouflaged as Bath Salts Has Dangerous, Bizarre Effects"
1694:"Mechanism of action of cathinone: the active ingredient of khat (Catha edulis)"
1503:
1357:(CoA), just like the beginning of the beta-oxidative pathway. It then undergoes
1330:
1293:
1277:
1273:
1147:
1115:
788:
1971:"What you need to know about flakka, the latest drug causing erratic behaviour"
1150:
molecule, it can easily cross cell membranes and other barriers, including the
853:
The table below shows the legality of khat and cathinone in various countries:
737:
region of the world for thousands of years. It is most commonly chewed for the
9445:
9380:
9360:
9355:
9350:
9345:
9325:
9315:
9289:
9268:
9223:
9218:
9187:
9156:
9141:
9131:
9045:
8876:
8839:
8829:
8809:
8769:
8759:
8614:
8610:
8600:
8396:
8346:
8341:
8273:
8263:
8248:
8243:
8233:
8164:
8135:
8130:
8003:
7937:
7920:
7831:
7826:
7796:
7286:
7227:
7010:
7005:
6960:
6950:
6940:
6850:
6840:
6769:
6764:
6598:
6593:
6578:
6447:
6443:
6400:
6369:
6349:
6317:
6267:
6236:
6141:
6136:
6084:
6079:
6023:
6018:
6008:
5866:
5861:
5846:
5831:
5704:
5694:
5665:
5605:
5573:
5563:
5538:
5468:
5438:
5428:
5383:
5378:
5322:
5317:
5307:
5133:
5118:
5108:
5058:
5028:
5023:
4993:
4983:
4908:
4873:
4654:
4561:
4538:
4267:
4257:
4184:
4174:
4149:
4144:
4129:
4056:
4036:
4031:
3986:
3926:
3916:
3906:
3873:
3729:
3719:
3710:
3700:
3695:
3660:
3650:
3645:
3591:
3576:
3546:
3522:
3507:
3499:
3494:
3464:
3434:
3419:
3404:
3345:
3335:
3217:
3212:
3202:
3164:
3159:
3126:
3121:
3091:
3083:
2973:
2890:
2860:
2850:
2800:
2795:
2699:
2659:
2601:
2596:
2581:
2518:
2508:
2460:
2402:
2397:
2392:
2384:
1425:
1354:
1337:. Both of these molecules can be converted to 1-phenylpropane-1,2-dione by a
755:
703:
494:
311:
5192:
2328:
2050:"НАРЕДБА за реда за класифициране на растенията и веществата като наркотични"
1710:
1693:
1543:
Other cathinone derivatives are strong psychoactive drugs. One such drug is
1154:. This property allows it to interact with the monoamine transporters in the
982:
Khat is illegal but a derivative of cathinone is available upon prescription
902:
Khat is legal but cathinone and cathine are classified as Class C substances
9425:
9320:
9233:
9213:
9146:
9035:
8866:
8834:
8774:
8283:
8253:
8204:
8189:
8125:
7852:
7811:
7442:
7437:
7432:
7427:
7422:
7306:
7301:
7274:
7248:
7202:
7197:
7015:
6728:
6623:
6608:
6354:
6312:
6241:
6191:
5896:
5876:
5655:
5568:
5543:
5488:
5168:
5143:
5008:
4978:
4968:
4893:
4759:
4609:
4599:
4533:
4523:
4370:
4360:
4237:
4232:
4227:
4222:
4217:
3779:
3685:
3670:
3655:
3606:
3561:
3380:
3184:
3174:
3169:
3149:
3106:
3033:
2953:
2948:
2938:
2923:
2895:
2875:
2870:
2840:
2805:
2732:
2727:
2722:
2626:
2611:
2606:
2538:
2475:
2455:
2407:
2376:
1560:
1544:
1533:
1269:
1135:
1123:
838:
The sale of khat is legal in some jurisdictions, but illegal in others (see
710:
676:
660:
640:
4433:
4428:
2263:"4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, Psilocin"
2247:
1895:
1862:
1719:
1673:
741:
effect it produces. The active ingredient was first proposed in 1930, when
2146:
1769:
29:
9430:
9276:
9116:
9097:
8927:
8917:
8861:
8856:
8794:
8664:
8654:
8644:
8421:
8313:
8238:
7786:
7321:
7101:
6925:
6920:
6870:
6860:
6759:
6487:
6461:
6456:
6390:
6359:
6231:
6201:
6146:
6028:
6003:
5967:
5962:
5760:
5734:
5729:
5660:
5533:
5503:
5443:
5327:
5302:
5266:
5261:
5179:
5043:
5003:
4963:
4958:
4754:
4385:
4345:
4192:
4139:
4134:
4081:
4076:
4066:
3951:
3853:
3799:
3640:
3541:
3484:
3222:
3197:
3141:
3111:
2998:
2968:
2963:
2918:
2830:
2810:
2717:
2674:
2631:
2558:
2450:
1761:
1342:
1297:
1258:
1163:
1111:
800:
796:
792:
738:
694:. Other phenethylamines that share this structure include the stimulants
643:
291:
300:
9470:
9435:
9365:
9126:
8528:
8493:
8174:
8098:
8083:
7729:
7694:
7684:
7674:
7669:
7664:
7654:
6151:
5448:
5158:
5083:
5038:
4739:
4734:
4729:
4719:
4714:
4709:
4704:
4699:
4694:
4689:
4684:
4624:
4581:
4553:
4413:
4335:
4325:
4212:
3571:
3454:
3330:
3131:
3053:
3048:
3043:
2933:
2928:
2621:
2591:
2171:
2138:
1522:
1264:
There are other effects not related to the CNS. The chewer can develop
1207:
1159:
763:
742:
664:
266:
37:
9385:
9305:
9170:
9161:
9102:
8605:
8523:
8513:
8503:
8488:
8478:
8473:
8078:
7978:
7781:
7759:
7754:
7634:
7629:
7624:
7609:
7604:
7599:
7574:
7539:
7534:
7529:
7524:
7519:
7514:
7509:
6825:
6815:
6251:
5821:
5163:
5113:
5098:
4679:
4674:
4669:
4614:
3551:
3535:
3531:
3527:
3063:
2988:
2576:
2571:
2566:
1854:
1514:
1511:
1487:
1445:
1412:
Cathinone can be synthetically produced from propiophenone through a
1215:
688:
391:
560:
InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3/t7-/m0/s1
775:
360:
9420:
8578:
8498:
8468:
8018:
7968:
7963:
7836:
7764:
7589:
7554:
7494:
7479:
7372:
7030:
6895:
6738:
6723:
6697:
6677:
6563:
5826:
5615:
4938:
4858:
4207:
4124:
3843:
3680:
3305:
3260:
2586:
1459:
1312:
1300:
and a great urge to use the drug for at least the first two days.
1186:
1143:
774:
751:
747:
687:. Cathinone differs from many other amphetamines in that it has a
647:
517:
508:
371:
1638:
Toennes SW, Harder S, Schramm M, Niess C, Kauert GF (July 2003).
1272:
after a khat session. Long-term effects of cathinone can include
1146:
group attached by a two-carbon separator. Because cathinone is a
8932:
8563:
8518:
8483:
7983:
7973:
7769:
7594:
7579:
7569:
7559:
7549:
7544:
7504:
7499:
7489:
7484:
7469:
7449:
6985:
6915:
6733:
6702:
6692:
6287:
5635:
3754:
3300:
3280:
3101:
1570:
1548:
1526:
1521:(beta) position of the side chain. The corresponding substance
1361:
at the double bond. This product then loses the CoA to produce
839:
726:
699:
684:
656:
351:
181:
157:
7376:
5196:
2349:
169:
9405:
2345:
1885:"List of psychotropic substances under international control"
1046:
Illegal to obtain unless approved by a medical practitioner
611:
416:
620:
108:
2032:"Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü"
614:
608:
145:
1494:, especially as a free base isolated from plant matter.
1416:
acylation of propionic acid and benzene. The resulting
134:
121:
5933:
2300:
European
Monitoring Center for Drugs and Drug Addiction
2096:"Cathinone: History, Synthesis, and Human Applications"
1464:
Chemical structure of bupropion, a cathinone derivative
583:
2290:
2288:
1510:. Cathinone differs from amphetamine by possessing a
1110:
Cathinone has been found to stimulate the release of
623:
617:
605:
9298:
9059:
8948:
8885:
8697:
8627:
7951:
7410:
7261:
6656:
5931:
5230:
4851:
4778:
4580:
4552:
4394:
4266:
4183:
4100:
3236:
3183:
3140:
3082:
2909:
2741:
2708:
2640:
2557:
2494:
2421:
2383:
1238:
Feelings of euphoria that last for one to two hours
602:
506:
493:
466:
461:
442:
410:
390:
370:
350:
330:
310:
290:
265:
245:
217:
204:
196:
98:
93:
77:
58:
53:
6658:
5232:
3251:1-Methylamino-1-(3,4-methylenedioxyphenyl)propane
1915:. PBS NewsHour. 20 September 2012. Archived from
1321:The synthesis of cathinone in khat begins with L-
795:(where khat is said to have originated), Kenya,
279:
4276:1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine
1940:"Drugs and dance as Israelis blot out intifada"
1478:-bromopropiophenone (which is easily made from
1452:to form enantiomerically pure S-(-)-cathinone.
254:
1333:while the non-beta-oxidative pathway produces
7388:
5208:
2361:
1836:
1834:
1832:
1830:
1828:
1826:
1824:
1822:
1820:
1818:
1396:Racemic cathinone from propiophenone via the
675:. It is probably the main contributor to the
8:
1448:protecting group is removed by heating with
1384:Synthesize enantiomerically pure S-Cathinone
28:
2166:
2164:
1241:Discussion of serious issues and increased
7395:
7381:
7373:
6667:
5942:
5241:
5215:
5201:
5193:
2368:
2354:
2346:
453:
430:
319:
9512:Drugs acting on the cardiovascular system
2237:
2089:
2087:
2085:
2083:
2081:
1709:
1663:
339:
9522:Norepinephrine-dopamine releasing agents
2207:
2205:
2203:
2201:
2199:
2197:
1743:
1741:
1739:
1737:
1735:
1733:
1731:
1729:
1644:British Journal of Clinical Pharmacology
855:
5938:Tooltip Norepinephrine releasing agents
1687:
1685:
1683:
1587:
1406:Two mechanism of synthesizing Cathinone
557:
537:
426:
299:
231:
2060:(in Bulgarian). Republic of Bulgaria.
1894:. United Nations. 2003. Archived from
1750:Clinical Pharmacology and Therapeutics
1138:and share the general structure of an
444:
27:
2273:from the original on 7 September 2013
1892:International Narcotics Control Board
825:Convention on Psychotropic Substances
399:
379:
7:
2341:Cathinone Popularity Soars in Israel
1803:from the original on 12 October 2014
9401:Lysergic acid 2,4-dimethylazetidide
2296:"Synthetic cathinones drug profile"
1793:"Yemen's khat habit soaks up water"
1162:. Cathinone induces the release of
359:
270:
6663:Tooltip Serotonin releasing agents
2306:from the original on 17 March 2015
2182:from the original on 23 April 2015
2012:from the original on 3 August 2018
2002:"The rising tide of 'legal highs'"
974:Khat is prohibited as a stimulant
14:
5237:Tooltip Dopamine releasing agents
1547:, a drug structurally similar to
3246:1-(4-Methylphenyl)-2-aminobutane
2106:from the original on 4 July 2015
1656:10.1046/j.1365-2125.2003.01834.x
1468:Cathinone can be extracted from
1389:
1377:
819:Internationally, cathinone is a
598:
484:
478:
153:(Authorized scientific use only)
45:
36:
8332:N,alpha-Diethylphenylethylamine
7358:Monoamine metabolism modulators
4165:2-Phenyl-3,6-dimethylmorpholine
3859:N,alpha-Diethylphenylethylamine
2230:10.1590/S1415-47572011000400017
2067:from the original on 2017-08-27
1938:Urquhart C (4 September 2004).
1620:from the original on 2023-08-27
1482:). Because cathinone is both a
659:) and is chemically similar to
565:Key:PUAQLLVFLMYYJJ-ZETCQYMHSA-N
9497:Drugs not assigned an ATC code
4755:Troparil (β-CPT, WIN 35,065-2)
3361:2-Amino-1,2-dihydronaphthalene
2218:Genetics and Molecular Biology
1189:receptors, thereby inhibiting
783:Over 20 million people in the
487:
472:
1:
7342:Monoamine reuptake inhibitors
7338:Receptor/signaling modulators
2261:Shulgin A (7 December 2005).
237:-2-Amino-1-phenylpropan-1-one
7294:Adrenergic release blockers:
1698:East African Medical Journal
1436:) is used to chlorinate the
1172:dopamine receptor antagonist
1114:and inhibit the reuptake of
188:Psychotropic Schedule I
9396:Lysergic acid 2-butyl amide
4864:3,3-Diphenylcyclobutanamine
4404:2-Diphenylmethylpyrrolidine
4291:3,4-Dichloromethylphenidate
4286:2-Methyl-3-phenylpiperidine
1185:adrenergic) and activating
729:has been cultivated in the
9548:
9406:Lysergic acid diethylamide
5224:Monoamine releasing agents
3864:N,N-Dimethylphenethylamine
2094:Hugins KB (17 July 2014).
1540:to the main carbon chain.
1502:, in much the same way as
990:Illegal unless authorized
910:Khat is a protected plant
746:analyzed khat leaves from
462:Chemical and physical data
130:(Prohibited psychotropics)
20:
7330:
7236:
7175:
7094:
6778:
6747:
6716:
6670:
6531:
6480:
6042:
5991:
5945:
5794:
5753:
5341:
5290:
5244:
5177:
4572:Phenylpiracetam hydrazide
2436:8-Cyclopentyltheophylline
833:Controlled Substances Act
573:
548:
528:
222:
44:
35:
8296:(Dextromethamphetamine,
6629:Phthalimidopropiophenone
5902:Phthalimidopropiophenone
2901:Phthalimidopropiophenone
1969:Chai C (16 April 2015).
1791:Kirby A (7 April 2007).
1711:10.4314/eamj.v77i6.46651
1616:(published 2023-07-25).
1444:catalyst. Finally, the
1430:phosphorus pentachloride
1400:-brominated intermediate
850:" in the United States.
8950:Phenylalkylpyrrolidines
8872:Methylenedioxycathinone
8549:3,4-MDA (tenamfetamine)
4306:4-Methylmethylphenidate
4301:4-Fluoromethylphenidate
3415:β-Phenylmethamphetamine
3371:5-(2-Aminopropyl)indole
3306:4-Fluoromethamphetamine
3261:2-Fluoromethamphetamine
2866:Methylenedioxycathinone
1614:Diário Oficial da União
1490:, it is very likely to
1247:Very active imagination
831:added cathinone to the
7874:β-Methylphenethylamine
7868:α-Methylphenethylamine
4630:Dichloropane (RTI-111)
3440:3-Benzhydrylmorpholine
3410:β-Methylphenethylamine
3286:3-Fluoroethamphetamine
3271:2-Phenyl-3-aminobutane
2329:Erowid Cathinone Vault
2267:Ask Dr. Shulgin Online
2036:www.resmigazete.gov.tr
1692:Patel NB (June 2000).
1566:Central nervous system
1474:, or synthesized from
1465:
1318:
1282:cardiovascular disease
1128:central nervous system
844:Substituted cathinones
780:
117:(Prohibited substance)
9507:Amphetamine alkaloids
9065:(and close relatives)
8564:MDMA (midomafetamine)
7906:-Methylphenethylamine
7898:-Methylphenethylamine
7890:-Methylphenethylamine
7882:-Methylphenethylamine
7362:Monoamine neurotoxins
6986:MDMA (midomafetamine)
6333:Dextromethamphetamine
6288:MDMA (midomafetamine)
5636:MDMA (midomafetamine)
5589:Dextromethamphetamine
4745:Salicylmethylecgonine
4381:Serdexmethylphenidate
4110:3-Fluorophenmetrazine
3809:Dextromethamphetamine
3755:MDMA (midomafetamine)
3341:a-Ethylphenethylamine
2751:3-Fluoromethcathinone
2423:Adenosine antagonists
1843:Phytotherapy Research
1576:Substituted cathinone
1463:
1339:condensation reaction
1316:
1292:of cathinone include
778:
771:Cultural significance
23:substituted cathinone
9229:N,N-Dimethyldopamine
8887:Phenylisobutylamines
8584:Naphthylaminopropane
8269:Isopropylamphetamine
8259:4-Hydroxyamphetamine
6365:Naphthylaminopropane
6247:4-Hydroxyamphetamine
5892:Naphthylaminopropane
5549:4-Hydroxyamphetamine
5079:Naphthylaminopropane
4590:4-fluorotropacocaine
3681:5-Iodo-2-aminoindane
3676:4-Hydroxyamphetamine
3513:Dimethoxyamphetamine
3291:3-Methoxyamphetamine
2642:Arylcyclohexylamines
2441:8-Phenyltheophylline
2431:8-Chlorotheophylline
1762:10.1038/clpt.1994.69
1428:, S-alanine. Then,
1369:Synthetic production
1179:adrenergic receptors
9391:Lysergic acid amide
9137:Ethylnorepinephrine
8940:Phenylisobutylamine
8392:Phenylpropanolamine
8327:-Norpseudoephedrine
8298:Levomethamphetamine
8185:Dimethylamphetamine
6971:MDA (tenamfetamine)
6638:Levopropylhexedrine
6416:Phenylpropanolamine
6338:Levomethamphetamine
6278:MDA (tenamfetamine)
6172:Dimethylamphetamine
5983:Pseudophenmetrazine
5917:Levopropylhexedrine
5626:MDA (tenamfetamine)
5594:Levomethamphetamine
5484:Dimethylamphetamine
5282:Pseudophenmetrazine
4170:Pseudophenmetrazine
3982:Phenylpropanolamine
3902:-Norpseudoephedrine
3869:Naphthylamphetamine
3813:Levomethamphetamine
3740:MDA (tenamfetamine)
3582:Ethylnorepinephrine
3518:Dimethylamphetamine
3301:4-Fluoroamphetamine
3296:3-Methylamphetamine
3281:3-Fluoroamphetamine
3256:2-Fluoroamphetamine
2529:Levopropylhexedrine
1919:on 29 December 2012
1290:withdrawal symptoms
1152:blood–brain barrier
1134:are all considered
1106:Mechanism of action
32:
7847:Phenylethanolamine
4355:Dexmethylphenidate
4341:Isopropylphenidate
4296:4-Benzylpiperidine
4281:2-Benzylpiperidine
3691:Indanylamphetamine
2786:4-Methylpentedrone
2771:4-Methylbuphedrone
2334:2008-06-22 at the
2139:10.1007/BF00427108
2127:Psychopharmacology
2058:Ministry of Health
1950:on 8 November 2016
1517:atom (C=O) on the
1466:
1319:
1101:Biological effects
827:. Circa 1993, the
781:
637:β-keto-amphetamine
9484:
9483:
8825:N-Ethylpentedrone
8785:Dimethylcathinone
8407:Propylamphetamine
8150:Dextroamphetamine
7822:Methallylescaline
7370:
7369:
7365:
7257:
7256:
6652:
6651:
6434:Propylamphetamine
6258:Iofetamine (123I)
6105:Dextroamphetamine
5927:
5926:
5720:Propylamphetamine
5554:Iofetamine (123I)
5403:Dextroamphetamine
5190:
5189:
5129:Rubidium chloride
4600:Altropane (IACFT)
4514:Indapyrophenidone
4336:Methylnaphthidate
4102:Phenylmorpholines
4022:Propylamphetamine
3901:
3713:
3502:
3390:Dextroamphetamine
2881:N-Ethylbuphedrone
2821:Dimethylcathinone
2776:4-Methylcathinone
2534:Methylhexaneamine
1450:hydrochloric acid
1442:aluminum chloride
1222:Effects on health
1132:neurotransmitters
1098:
1097:
840:Khat (Regulation)
785:Arabian Peninsula
735:Arabian Peninsula
633:benzoylethanamine
591:
590:
540:O=C(c1ccccc1)(N)C
519:Interactive image
412:CompTox Dashboard
185:
173:
161:
148:
137:
125:
112:
16:Chemical compound
9539:
9532:Phenyl compounds
9190:
9182:
9173:
9164:
9105:
9066:
8820:N-Ethylhexedrone
8800:Hydroxybupropion
8640:Chlorphentermine
8617:
8326:
8304:Methoxyphenamine
8279:Lisdexamfetamine
8223:Levofenfluramine
7863:Phenpromethamine
7397:
7390:
7383:
7374:
7332:
7284:Antagonist-like:
6956:Levofenfluramine
6866:Chlorphentermine
6783:Phenethylamines:
6755:4-Methylaminorex
6668:
6664:
6660:
6619:Methylhexanamine
6450:
6406:Phenpromethamine
6263:Lisdexamfetamine
6047:Phenethylamines:
5943:
5939:
5935:
5887:Methylhexanamine
5710:Phenpromethamine
5559:Lisdexamfetamine
5346:Phenethylamines:
5242:
5238:
5234:
5217:
5210:
5203:
5194:
4610:CFT (WIN 35,428)
4595:4'-Fluorococaine
4459:Diphenylprolinol
4326:Ethylnaphthidate
4321:Diphenylpyraline
3962:Phenpromethamine
3899:
3834:Methoxyphenamine
3824:Methoxyphenamine
3725:Lisdexamfetamine
3711:
3625:Levofenfluramine
3500:
3460:Chlorphentermine
3193:4-Methylaminorex
2886:N-Ethylhexedrone
2370:
2363:
2356:
2347:
2316:
2315:
2313:
2311:
2292:
2283:
2282:
2280:
2278:
2258:
2252:
2251:
2241:
2209:
2192:
2191:
2189:
2187:
2168:
2159:
2158:
2122:
2116:
2115:
2113:
2111:
2091:
2076:
2075:
2073:
2072:
2066:
2055:
2046:
2040:
2039:
2028:
2022:
2021:
2019:
2017:
1997:
1991:
1990:
1988:
1986:
1981:on 20 April 2015
1977:. Archived from
1966:
1960:
1959:
1957:
1955:
1946:. Archived from
1935:
1929:
1928:
1926:
1924:
1909:
1903:
1902:
1900:
1889:
1881:
1875:
1874:
1855:10.1002/ptr.1106
1838:
1813:
1812:
1810:
1808:
1788:
1782:
1781:
1745:
1724:
1723:
1713:
1689:
1678:
1677:
1667:
1635:
1629:
1628:
1626:
1625:
1602:
1596:
1592:
1423:optically active
1393:
1381:
1345:and producing CO
1255:loss of appetite
856:
779:Man chewing khat
767:in khat leaves.
692:functional group
683:, also known as
631:; also known as
630:
629:
626:
625:
622:
619:
616:
613:
610:
607:
604:
587:
586:
579:
521:
501:
489:
486:
480:
474:
457:
446:
435:
434:
420:
418:
403:
383:
363:
343:
323:
303:
283:
273:
272:
258:
209:
183:
180:
171:
168:
159:
156:
147:
144:
136:
133:
123:
120:
110:
107:
49:
40:
33:
31:
9547:
9546:
9542:
9541:
9540:
9538:
9537:
9536:
9487:
9486:
9485:
9480:
9416:Methoxphenidine
9294:
9259:Normetanephrine
9188:
9180:
9171:
9162:
9103:
9064:
9063:
9055:
8944:
8935:
8881:
8842:
8693:
8684:
8672:
8623:
8615:
8591:
8439:
8427:Tranylcypromine
8412:Pseudoephedrine
8324:
8319:Norfenfluramine
8294:Methamphetamine
8219:Dexfenfluramine
8154:Levoamphetamine
8101:
7999:Bromo-DragonFLY
7947:
7933:
7911:Methylphenidate
7842:
7412:Phenethylamines
7406:
7404:Phenethylamines
7401:
7371:
7366:
7326:
7269:DAT modulators:
7253:
7232:
7171:
7090:
7046:Norfenfluramine
6891:Dexfenfluramine
6774:
6743:
6721:Aminotetralins:
6712:
6662:
6648:
6634:Propylhexedrine
6527:
6476:
6448:
6439:Pseudoephedrine
6328:Methamphetamine
6110:Levoamphetamine
6038:
5987:
5973:Phendimetrazine
5937:
5923:
5912:Propylhexedrine
5907:Phenylbiguanide
5790:
5749:
5725:Pseudoephedrine
5584:Methamphetamine
5408:Levoamphetamine
5337:
5286:
5272:Phendimetrazine
5236:
5226:
5221:
5191:
5186:
5173:
5074:Methiopropamine
4847:
4774:
4700:RTI-121 (IPCIT)
4576:
4567:Phenylpiracetam
4548:
4390:
4376:Propylphenidate
4351:Methylphenidate
4311:Desoxypipradrol
4262:
4179:
4155:Phendimetrazine
4096:
4072:Tranylcypromine
4027:Pseudoephedrine
3894:Normetanephrine
3889:Norfenfluramine
3805:Methamphetamine
3621:Dexfenfluramine
3394:Levoamphetamine
3376:2-Aminotetralin
3238:Phenethylamines
3232:
3179:
3136:
3078:
2905:
2846:Isoethcathinone
2737:
2704:
2636:
2553:
2544:Propylhexedrine
2490:
2417:
2379:
2374:
2336:Wayback Machine
2325:
2320:
2319:
2309:
2307:
2294:
2293:
2286:
2276:
2274:
2260:
2259:
2255:
2211:
2210:
2195:
2185:
2183:
2170:
2169:
2162:
2124:
2123:
2119:
2109:
2107:
2093:
2092:
2079:
2070:
2068:
2064:
2053:
2048:
2047:
2043:
2030:
2029:
2025:
2015:
2013:
2006:Chemistry World
1999:
1998:
1994:
1984:
1982:
1968:
1967:
1963:
1953:
1951:
1937:
1936:
1932:
1922:
1920:
1911:
1910:
1906:
1898:
1887:
1883:
1882:
1878:
1840:
1839:
1816:
1806:
1804:
1790:
1789:
1785:
1747:
1746:
1727:
1691:
1690:
1681:
1637:
1636:
1632:
1623:
1621:
1604:
1603:
1599:
1593:
1589:
1584:
1557:
1508:methamphetamine
1458:
1438:carboxylic acid
1435:
1410:
1409:
1408:
1407:
1403:
1402:
1401:
1394:
1386:
1385:
1382:
1371:
1348:
1311:
1306:
1224:
1212:small intestine
1206:and one in the
1199:
1184:
1108:
1103:
835:'s Schedule I.
823:drug under the
817:
773:
724:
719:
601:
597:
582:
580:
577:(what is this?)
574:
569:
566:
561:
556:
555:
544:
541:
536:
535:
524:
499:
483:
477:
438:
414:
406:
386:
366:
346:
326:
306:
286:
269:
261:
241:
238:
230:
229:
207:
198:Pharmacokinetic
192:
89:
61:
26:
17:
12:
11:
5:
9545:
9543:
9535:
9534:
9529:
9524:
9519:
9514:
9509:
9504:
9499:
9489:
9488:
9482:
9481:
9479:
9478:
9473:
9468:
9463:
9458:
9453:
9450:Levosalbutamol
9443:
9438:
9433:
9428:
9423:
9418:
9413:
9408:
9403:
9398:
9393:
9388:
9383:
9378:
9373:
9368:
9363:
9358:
9353:
9348:
9343:
9338:
9333:
9331:Desvenlafaxine
9328:
9323:
9318:
9313:
9308:
9302:
9300:
9296:
9295:
9293:
9292:
9287:
9282:
9274:
9266:
9261:
9256:
9246:
9244:Norepinephrine
9241:
9231:
9226:
9221:
9216:
9211:
9206:
9201:
9193:
9185:
9183:-Phenylalanine
9177:
9168:
9159:
9154:
9149:
9144:
9139:
9134:
9129:
9124:
9119:
9114:
9109:
9100:
9095:
9090:
9085:
9080:
9075:
9069:
9067:
9061:Catecholamines
9057:
9056:
9054:
9053:
9048:
9043:
9038:
9033:
9028:
9023:
9018:
9013:
9008:
9003:
8998:
8993:
8988:
8983:
8978:
8973:
8968:
8963:
8954:
8952:
8946:
8945:
8943:
8942:
8930:
8925:
8920:
8915:
8910:
8905:
8900:
8891:
8889:
8883:
8882:
8880:
8879:
8874:
8869:
8864:
8859:
8854:
8849:
8837:
8832:
8827:
8822:
8817:
8812:
8807:
8802:
8797:
8792:
8787:
8782:
8777:
8772:
8767:
8762:
8757:
8752:
8747:
8742:
8737:
8732:
8727:
8722:
8717:
8712:
8703:
8701:
8695:
8694:
8692:
8691:
8679:
8667:
8662:
8657:
8652:
8647:
8642:
8633:
8631:
8625:
8624:
8622:
8621:
8608:
8603:
8598:
8586:
8581:
8576:
8574:Methamnetamine
8571:
8566:
8561:
8556:
8551:
8546:
8541:
8536:
8531:
8526:
8521:
8516:
8511:
8506:
8501:
8496:
8491:
8486:
8481:
8476:
8471:
8466:
8461:
8456:
8451:
8446:
8434:
8429:
8424:
8419:
8414:
8409:
8404:
8399:
8394:
8389:
8384:
8379:
8374:
8369:
8364:
8359:
8354:
8349:
8344:
8339:
8334:
8329:
8321:
8316:
8311:
8306:
8301:
8291:
8286:
8281:
8276:
8271:
8266:
8261:
8256:
8251:
8246:
8241:
8236:
8231:
8226:
8212:
8207:
8202:
8197:
8195:Etilamfetamine
8192:
8187:
8182:
8177:
8172:
8167:
8162:
8157:
8143:
8138:
8133:
8128:
8123:
8118:
8113:
8108:
8096:
8091:
8086:
8081:
8076:
8071:
8066:
8061:
8056:
8051:
8046:
8041:
8036:
8031:
8026:
8021:
8016:
8011:
8006:
8001:
7996:
7991:
7986:
7981:
7976:
7971:
7966:
7957:
7955:
7949:
7948:
7946:
7945:
7940:
7928:
7923:
7914:
7913:
7908:
7900:
7892:
7884:
7876:
7871:
7865:
7860:
7858:Phenethylamine
7855:
7840:
7839:
7834:
7829:
7824:
7819:
7814:
7809:
7804:
7799:
7794:
7789:
7784:
7779:
7773:
7772:
7767:
7762:
7757:
7752:
7747:
7742:
7737:
7732:
7727:
7722:
7717:
7712:
7707:
7702:
7697:
7692:
7687:
7682:
7677:
7672:
7667:
7662:
7657:
7652:
7647:
7642:
7637:
7632:
7627:
7622:
7617:
7612:
7607:
7602:
7597:
7592:
7587:
7582:
7577:
7572:
7567:
7562:
7557:
7552:
7547:
7542:
7537:
7532:
7527:
7522:
7517:
7512:
7507:
7502:
7497:
7492:
7487:
7482:
7477:
7472:
7467:
7462:
7457:
7452:
7446:
7445:
7440:
7435:
7430:
7425:
7416:
7414:
7408:
7407:
7402:
7400:
7399:
7392:
7385:
7377:
7368:
7367:
7331:
7328:
7327:
7325:
7324:
7319:
7314:
7309:
7304:
7299:
7290:
7289:
7277:
7265:
7263:
7259:
7258:
7255:
7254:
7252:
7251:
7246:
7237:
7234:
7233:
7231:
7230:
7225:
7220:
7215:
7210:
7205:
7200:
7195:
7190:
7185:
7176:
7173:
7172:
7170:
7169:
7164:
7159:
7154:
7149:
7144:
7139:
7134:
7129:
7124:
7119:
7114:
7109:
7104:
7095:
7092:
7091:
7089:
7088:
7083:
7078:
7073:
7068:
7063:
7058:
7053:
7048:
7043:
7038:
7033:
7028:
7023:
7018:
7013:
7008:
7003:
6998:
6993:
6988:
6983:
6978:
6973:
6968:
6963:
6958:
6953:
6948:
6943:
6938:
6933:
6928:
6923:
6918:
6913:
6908:
6903:
6898:
6893:
6888:
6883:
6881:Metamfepramone
6878:
6873:
6868:
6863:
6858:
6853:
6848:
6843:
6838:
6833:
6828:
6823:
6818:
6813:
6808:
6803:
6798:
6793:
6788:
6779:
6776:
6775:
6773:
6772:
6767:
6762:
6757:
6748:
6745:
6744:
6742:
6741:
6736:
6731:
6726:
6717:
6714:
6713:
6711:
6710:
6705:
6700:
6695:
6690:
6685:
6680:
6671:
6665:
6654:
6653:
6650:
6649:
6647:
6646:
6644:Tuaminoheptane
6641:
6631:
6626:
6621:
6616:
6611:
6606:
6601:
6596:
6591:
6586:
6581:
6576:
6574:Cyclopentamine
6571:
6566:
6561:
6556:
6551:
6546:
6541:
6532:
6529:
6528:
6526:
6525:
6520:
6515:
6510:
6505:
6500:
6495:
6490:
6481:
6478:
6477:
6475:
6474:
6469:
6464:
6459:
6454:
6441:
6436:
6431:
6426:
6418:
6413:
6408:
6403:
6398:
6396:Phenethylamine
6393:
6388:
6380:
6372:
6367:
6362:
6357:
6352:
6347:
6342:
6341:
6340:
6335:
6325:
6320:
6315:
6310:
6305:
6300:
6295:
6293:Metamfepramone
6290:
6285:
6280:
6275:
6270:
6265:
6260:
6255:
6249:
6244:
6239:
6234:
6229:
6224:
6219:
6214:
6209:
6207:Etilamfetamine
6204:
6199:
6194:
6189:
6184:
6179:
6174:
6169:
6164:
6159:
6154:
6149:
6144:
6139:
6134:
6129:
6124:
6119:
6114:
6113:
6112:
6107:
6097:
6092:
6087:
6082:
6077:
6072:
6067:
6062:
6057:
6052:
6043:
6040:
6039:
6037:
6036:
6031:
6026:
6021:
6016:
6011:
6006:
6001:
5992:
5989:
5988:
5986:
5985:
5980:
5975:
5970:
5965:
5960:
5955:
5946:
5940:
5929:
5928:
5925:
5924:
5922:
5921:
5920:
5919:
5909:
5904:
5899:
5894:
5889:
5884:
5879:
5874:
5869:
5864:
5859:
5854:
5849:
5844:
5842:Cyclopentamine
5839:
5834:
5829:
5824:
5819:
5814:
5809:
5804:
5795:
5792:
5791:
5789:
5788:
5783:
5778:
5773:
5768:
5763:
5754:
5751:
5750:
5748:
5747:
5742:
5737:
5732:
5727:
5722:
5717:
5712:
5707:
5702:
5700:Phenethylamine
5697:
5692:
5684:
5676:
5668:
5663:
5658:
5653:
5648:
5643:
5638:
5633:
5628:
5623:
5618:
5613:
5608:
5603:
5598:
5597:
5596:
5591:
5581:
5579:Metamfepramone
5576:
5571:
5566:
5561:
5556:
5551:
5546:
5541:
5536:
5531:
5526:
5521:
5516:
5511:
5509:Etilamfetamine
5506:
5501:
5496:
5491:
5486:
5481:
5476:
5471:
5466:
5461:
5456:
5451:
5446:
5441:
5436:
5431:
5426:
5421:
5416:
5411:
5405:
5396:
5391:
5386:
5381:
5376:
5371:
5366:
5361:
5356:
5351:
5342:
5339:
5338:
5336:
5335:
5330:
5325:
5320:
5315:
5310:
5305:
5300:
5291:
5288:
5287:
5285:
5284:
5279:
5274:
5269:
5264:
5259:
5254:
5245:
5239:
5228:
5227:
5222:
5220:
5219:
5212:
5205:
5197:
5188:
5187:
5178:
5175:
5174:
5172:
5171:
5166:
5161:
5156:
5151:
5146:
5141:
5136:
5131:
5126:
5121:
5116:
5111:
5106:
5101:
5096:
5091:
5086:
5081:
5076:
5071:
5069:Methastyridone
5066:
5064:Methamnetamine
5061:
5056:
5051:
5046:
5041:
5036:
5031:
5026:
5021:
5016:
5011:
5006:
5001:
4996:
4991:
4986:
4981:
4976:
4971:
4966:
4961:
4956:
4951:
4946:
4941:
4936:
4931:
4926:
4921:
4916:
4911:
4906:
4901:
4896:
4891:
4886:
4881:
4876:
4871:
4869:Amfonelic acid
4866:
4861:
4855:
4853:
4849:
4848:
4846:
4845:
4840:
4835:
4830:
4825:
4820:
4815:
4810:
4805:
4800:
4795:
4790:
4784:
4782:
4776:
4775:
4773:
4772:
4767:
4762:
4757:
4752:
4747:
4742:
4737:
4732:
4727:
4722:
4717:
4712:
4707:
4702:
4697:
4692:
4687:
4682:
4677:
4672:
4667:
4662:
4657:
4652:
4647:
4642:
4637:
4632:
4627:
4622:
4617:
4615:β-CIT (RTI-55)
4612:
4607:
4602:
4597:
4592:
4586:
4584:
4578:
4577:
4575:
4574:
4569:
4564:
4558:
4556:
4550:
4549:
4547:
4546:
4541:
4536:
4531:
4526:
4521:
4516:
4511:
4506:
4501:
4496:
4491:
4486:
4481:
4476:
4471:
4466:
4461:
4456:
4451:
4446:
4441:
4436:
4431:
4426:
4421:
4416:
4411:
4406:
4400:
4398:
4392:
4391:
4389:
4388:
4383:
4378:
4373:
4368:
4363:
4358:
4348:
4343:
4338:
4333:
4331:Ethylphenidate
4328:
4323:
4318:
4313:
4308:
4303:
4298:
4293:
4288:
4283:
4278:
4272:
4270:
4264:
4263:
4261:
4260:
4255:
4250:
4245:
4240:
4235:
4230:
4225:
4220:
4215:
4210:
4205:
4200:
4195:
4189:
4187:
4181:
4180:
4178:
4177:
4172:
4167:
4162:
4157:
4152:
4147:
4142:
4137:
4132:
4127:
4122:
4117:
4112:
4106:
4104:
4098:
4097:
4095:
4094:
4089:
4084:
4079:
4074:
4069:
4064:
4059:
4054:
4049:
4044:
4041:Levosalbutamol
4034:
4029:
4024:
4019:
4014:
4009:
4004:
3999:
3994:
3989:
3984:
3979:
3974:
3969:
3964:
3959:
3954:
3949:
3944:
3939:
3934:
3929:
3924:
3919:
3914:
3909:
3904:
3896:
3891:
3886:
3881:
3879:Norepinephrine
3876:
3871:
3866:
3861:
3856:
3851:
3846:
3841:
3836:
3831:
3826:
3821:
3816:
3802:
3797:
3792:
3787:
3782:
3777:
3772:
3767:
3762:
3757:
3752:
3747:
3742:
3737:
3732:
3727:
3722:
3717:
3708:
3703:
3698:
3693:
3688:
3683:
3678:
3673:
3668:
3663:
3658:
3653:
3648:
3643:
3638:
3633:
3628:
3614:
3609:
3604:
3599:
3594:
3589:
3587:Etilamfetamine
3584:
3579:
3574:
3569:
3564:
3559:
3554:
3549:
3544:
3539:
3525:
3520:
3515:
3510:
3505:
3497:
3492:
3487:
3482:
3477:
3472:
3467:
3462:
3457:
3452:
3447:
3442:
3437:
3432:
3427:
3422:
3417:
3412:
3407:
3402:
3397:
3383:
3378:
3373:
3368:
3363:
3358:
3353:
3348:
3343:
3338:
3333:
3328:
3323:
3318:
3313:
3308:
3303:
3298:
3293:
3288:
3283:
3278:
3273:
3268:
3263:
3258:
3253:
3248:
3242:
3240:
3234:
3233:
3231:
3230:
3225:
3220:
3215:
3210:
3205:
3200:
3195:
3189:
3187:
3181:
3180:
3178:
3177:
3172:
3167:
3162:
3157:
3152:
3146:
3144:
3138:
3137:
3135:
3134:
3129:
3124:
3119:
3114:
3109:
3104:
3099:
3094:
3088:
3086:
3080:
3079:
3077:
3076:
3071:
3066:
3061:
3056:
3051:
3046:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
3001:
2996:
2991:
2986:
2981:
2976:
2971:
2966:
2961:
2956:
2951:
2946:
2941:
2936:
2931:
2926:
2921:
2915:
2913:
2907:
2906:
2904:
2903:
2898:
2893:
2888:
2883:
2878:
2873:
2868:
2863:
2858:
2853:
2848:
2843:
2838:
2833:
2828:
2823:
2818:
2813:
2808:
2803:
2798:
2793:
2788:
2783:
2778:
2773:
2768:
2763:
2758:
2753:
2747:
2745:
2739:
2738:
2736:
2735:
2730:
2725:
2720:
2714:
2712:
2706:
2705:
2703:
2702:
2697:
2692:
2687:
2682:
2677:
2672:
2667:
2662:
2657:
2655:Dieticyclidine
2652:
2646:
2644:
2638:
2637:
2635:
2634:
2629:
2624:
2619:
2614:
2609:
2604:
2599:
2594:
2589:
2584:
2579:
2574:
2569:
2563:
2561:
2555:
2554:
2552:
2551:
2549:Tuaminoheptane
2546:
2541:
2536:
2531:
2526:
2521:
2516:
2511:
2506:
2504:Cyclopentamine
2500:
2498:
2492:
2491:
2489:
2488:
2483:
2478:
2473:
2468:
2466:Istradefylline
2463:
2458:
2453:
2448:
2443:
2438:
2433:
2427:
2425:
2419:
2418:
2416:
2415:
2410:
2405:
2400:
2395:
2389:
2387:
2381:
2380:
2375:
2373:
2372:
2365:
2358:
2350:
2344:
2343:
2338:
2324:
2323:External links
2321:
2318:
2317:
2284:
2253:
2224:(4): 640–646.
2193:
2160:
2133:(3): 269–270.
2117:
2077:
2041:
2023:
1992:
1961:
1930:
1904:
1901:on 2012-08-31.
1876:
1849:(5): 403–413.
1814:
1783:
1756:(5): 556–562.
1725:
1704:(6): 329–332.
1679:
1650:(1): 125–130.
1630:
1608:(2023-07-24).
1597:
1586:
1585:
1583:
1580:
1579:
1578:
1573:
1568:
1563:
1556:
1553:
1506:is related to
1457:
1454:
1433:
1414:Friedel-Crafts
1405:
1404:
1395:
1388:
1387:
1383:
1376:
1375:
1374:
1373:
1372:
1370:
1367:
1346:
1310:
1307:
1305:
1302:
1262:
1261:
1253:Irritability,
1251:
1248:
1245:
1239:
1228:antidepressant
1223:
1220:
1198:
1195:
1182:
1156:synaptic cleft
1120:norepinephrine
1107:
1104:
1102:
1099:
1096:
1095:
1092:
1088:
1087:
1084:
1080:
1079:
1076:
1072:
1071:
1068:
1064:
1063:
1060:
1056:
1055:
1052:
1048:
1047:
1044:
1040:
1039:
1036:
1035:United Kingdom
1032:
1031:
1028:
1024:
1023:
1020:
1016:
1015:
1012:
1008:
1007:
1004:
1000:
999:
996:
992:
991:
988:
984:
983:
980:
976:
975:
972:
968:
967:
964:
960:
959:
956:
952:
951:
948:
944:
943:
940:
936:
935:
932:
928:
927:
924:
920:
919:
916:
912:
911:
908:
904:
903:
900:
896:
895:
892:
888:
887:
884:
880:
879:
876:
872:
871:
868:
864:
863:
860:
816:
813:
772:
769:
731:Horn of Africa
723:
720:
718:
715:
708:antidepressant
589:
588:
571:
570:
568:
567:
564:
562:
559:
551:
550:
549:
546:
545:
543:
542:
539:
531:
530:
529:
526:
525:
523:
522:
514:
512:
504:
503:
497:
491:
490:
481:
475:
470:
464:
463:
459:
458:
448:
440:
439:
437:
436:
423:
421:
408:
407:
405:
404:
396:
394:
388:
387:
385:
384:
376:
374:
368:
367:
365:
364:
356:
354:
348:
347:
345:
344:
336:
334:
328:
327:
325:
324:
316:
314:
308:
307:
305:
304:
296:
294:
288:
287:
285:
284:
276:
274:
263:
262:
260:
259:
251:
249:
243:
242:
240:
239:
233:
225:
224:
223:
220:
219:
215:
214:
211:
202:
201:
194:
193:
191:
190:
178:
166:
154:
142:
131:
118:
104:
102:
96:
95:
91:
90:
88:
87:
83:
81:
75:
74:
73:: Low–moderate
64:
56:
55:
51:
50:
42:
41:
15:
13:
10:
9:
6:
4:
3:
2:
9544:
9533:
9530:
9528:
9525:
9523:
9520:
9518:
9515:
9513:
9510:
9508:
9505:
9503:
9500:
9498:
9495:
9494:
9492:
9477:
9474:
9472:
9469:
9467:
9466:Thiamphenicol
9464:
9462:
9461:Theodrenaline
9459:
9457:
9454:
9451:
9447:
9444:
9442:
9439:
9437:
9434:
9432:
9429:
9427:
9424:
9422:
9419:
9417:
9414:
9412:
9409:
9407:
9404:
9402:
9399:
9397:
9394:
9392:
9389:
9387:
9384:
9382:
9379:
9377:
9376:Fluorolintane
9374:
9372:
9369:
9367:
9364:
9362:
9359:
9357:
9354:
9352:
9349:
9347:
9344:
9342:
9339:
9337:
9334:
9332:
9329:
9327:
9324:
9322:
9319:
9317:
9314:
9312:
9309:
9307:
9304:
9303:
9301:
9299:Miscellaneous
9297:
9291:
9288:
9286:
9285:Phenylephrine
9283:
9281:
9279:
9275:
9273:
9271:
9267:
9265:
9264:Orciprenaline
9262:
9260:
9257:
9254:
9250:
9247:
9245:
9242:
9239:
9238:Levonordefrin
9235:
9232:
9230:
9227:
9225:
9222:
9220:
9217:
9215:
9212:
9210:
9207:
9205:
9202:
9200:
9198:
9194:
9192:
9186:
9184:
9178:
9175:
9169:
9166:
9160:
9158:
9155:
9153:
9150:
9148:
9145:
9143:
9140:
9138:
9135:
9133:
9130:
9128:
9125:
9123:
9120:
9118:
9115:
9113:
9110:
9107:
9101:
9099:
9096:
9094:
9091:
9089:
9086:
9084:
9081:
9079:
9076:
9074:
9071:
9070:
9068:
9062:
9058:
9052:
9049:
9047:
9044:
9042:
9039:
9037:
9034:
9032:
9029:
9027:
9024:
9022:
9019:
9017:
9014:
9012:
9009:
9007:
9004:
9002:
8999:
8997:
8994:
8992:
8989:
8987:
8984:
8982:
8979:
8977:
8974:
8972:
8969:
8967:
8964:
8962:
8959:
8956:
8955:
8953:
8951:
8947:
8941:
8938:
8934:
8931:
8929:
8926:
8924:
8921:
8919:
8916:
8914:
8911:
8909:
8906:
8904:
8901:
8899:
8896:
8893:
8892:
8890:
8888:
8884:
8878:
8875:
8873:
8870:
8868:
8865:
8863:
8860:
8858:
8855:
8853:
8850:
8848:
8845:
8841:
8838:
8836:
8833:
8831:
8828:
8826:
8823:
8821:
8818:
8816:
8813:
8811:
8808:
8806:
8805:Methcathinone
8803:
8801:
8798:
8796:
8793:
8791:
8788:
8786:
8783:
8781:
8778:
8776:
8773:
8771:
8768:
8766:
8763:
8761:
8758:
8756:
8753:
8751:
8748:
8746:
8743:
8741:
8738:
8736:
8733:
8731:
8728:
8726:
8723:
8721:
8718:
8716:
8713:
8711:
8708:
8705:
8704:
8702:
8700:
8696:
8690:
8687:
8683:
8680:
8678:
8675:
8671:
8668:
8666:
8663:
8661:
8660:Mephentermine
8658:
8656:
8653:
8651:
8648:
8646:
8643:
8641:
8638:
8635:
8634:
8632:
8630:
8626:
8619:
8612:
8609:
8607:
8604:
8602:
8599:
8597:
8594:
8590:
8587:
8585:
8582:
8580:
8577:
8575:
8572:
8570:
8567:
8565:
8562:
8560:
8557:
8555:
8552:
8550:
8547:
8545:
8542:
8540:
8537:
8535:
8532:
8530:
8527:
8525:
8522:
8520:
8517:
8515:
8512:
8510:
8509:6-Chloro-MDMA
8507:
8505:
8502:
8500:
8497:
8495:
8492:
8490:
8487:
8485:
8482:
8480:
8477:
8475:
8472:
8470:
8467:
8465:
8462:
8460:
8457:
8455:
8452:
8450:
8447:
8445:
8442:
8438:
8435:
8433:
8432:Xylopropamine
8430:
8428:
8425:
8423:
8420:
8418:
8415:
8413:
8410:
8408:
8405:
8403:
8400:
8398:
8395:
8393:
8390:
8388:
8385:
8383:
8380:
8378:
8375:
8373:
8370:
8368:
8365:
8363:
8360:
8358:
8355:
8353:
8350:
8348:
8345:
8343:
8340:
8338:
8335:
8333:
8330:
8328:
8322:
8320:
8317:
8315:
8312:
8310:
8307:
8305:
8302:
8299:
8295:
8292:
8290:
8287:
8285:
8282:
8280:
8277:
8275:
8272:
8270:
8267:
8265:
8262:
8260:
8257:
8255:
8252:
8250:
8247:
8245:
8242:
8240:
8237:
8235:
8232:
8230:
8227:
8224:
8220:
8216:
8213:
8211:
8208:
8206:
8203:
8201:
8198:
8196:
8193:
8191:
8188:
8186:
8183:
8181:
8178:
8176:
8173:
8171:
8170:Benzphetamine
8168:
8166:
8163:
8161:
8158:
8155:
8151:
8147:
8144:
8142:
8139:
8137:
8134:
8132:
8129:
8127:
8124:
8122:
8119:
8117:
8114:
8112:
8109:
8107:
8104:
8100:
8097:
8095:
8092:
8090:
8087:
8085:
8082:
8080:
8077:
8075:
8072:
8070:
8067:
8065:
8062:
8060:
8057:
8055:
8052:
8050:
8047:
8045:
8042:
8040:
8037:
8035:
8032:
8030:
8027:
8025:
8022:
8020:
8017:
8015:
8012:
8010:
8007:
8005:
8002:
8000:
7997:
7995:
7992:
7990:
7987:
7985:
7982:
7980:
7977:
7975:
7972:
7970:
7967:
7965:
7962:
7961:Psychedelics:
7959:
7958:
7956:
7954:
7950:
7944:
7941:
7939:
7936:
7932:
7929:
7927:
7924:
7922:
7919:
7916:
7915:
7912:
7909:
7907:
7905:
7901:
7899:
7897:
7893:
7891:
7889:
7885:
7883:
7881:
7877:
7875:
7872:
7870:(amphetamine)
7869:
7866:
7864:
7861:
7859:
7856:
7854:
7851:
7850:
7849:
7848:
7845:
7838:
7835:
7833:
7830:
7828:
7825:
7823:
7820:
7818:
7815:
7813:
7810:
7808:
7805:
7803:
7800:
7798:
7795:
7793:
7792:Isoproscaline
7790:
7788:
7785:
7783:
7780:
7778:
7777:Allylescaline
7775:
7774:
7771:
7768:
7766:
7763:
7761:
7758:
7756:
7753:
7751:
7748:
7746:
7743:
7741:
7738:
7736:
7733:
7731:
7728:
7726:
7723:
7721:
7718:
7716:
7713:
7711:
7708:
7706:
7703:
7701:
7698:
7696:
7693:
7691:
7688:
7686:
7683:
7681:
7678:
7676:
7673:
7671:
7668:
7666:
7663:
7661:
7658:
7656:
7653:
7651:
7648:
7646:
7643:
7641:
7638:
7636:
7633:
7631:
7628:
7626:
7623:
7621:
7618:
7616:
7613:
7611:
7608:
7606:
7603:
7601:
7598:
7596:
7593:
7591:
7588:
7586:
7583:
7581:
7578:
7576:
7573:
7571:
7568:
7566:
7563:
7561:
7558:
7556:
7553:
7551:
7548:
7546:
7543:
7541:
7538:
7536:
7533:
7531:
7528:
7526:
7523:
7521:
7518:
7516:
7513:
7511:
7508:
7506:
7503:
7501:
7498:
7496:
7493:
7491:
7488:
7486:
7483:
7481:
7478:
7476:
7473:
7471:
7468:
7466:
7463:
7461:
7458:
7456:
7453:
7451:
7448:
7447:
7444:
7441:
7439:
7436:
7434:
7431:
7429:
7426:
7424:
7421:
7420:Psychedelics:
7418:
7417:
7415:
7413:
7409:
7405:
7398:
7393:
7391:
7386:
7384:
7379:
7378:
7375:
7364:
7363:
7359:
7355:
7354:Serotonergics
7351:
7350:Dopaminergics
7347:
7343:
7339:
7336:
7329:
7323:
7320:
7318:
7315:
7313:
7310:
7308:
7305:
7303:
7300:
7298:
7295:
7292:
7291:
7288:
7285:
7281:
7278:
7276:
7273:
7272:Agonist-like:
7270:
7267:
7266:
7264:
7260:
7250:
7247:
7245:
7242:
7239:
7238:
7235:
7229:
7226:
7224:
7221:
7219:
7216:
7214:
7211:
7209:
7206:
7204:
7201:
7199:
7196:
7194:
7191:
7189:
7186:
7184:
7181:
7178:
7177:
7174:
7168:
7165:
7163:
7160:
7158:
7155:
7153:
7150:
7148:
7145:
7143:
7140:
7138:
7135:
7133:
7130:
7128:
7125:
7123:
7120:
7118:
7115:
7113:
7110:
7108:
7105:
7103:
7100:
7097:
7096:
7093:
7087:
7084:
7082:
7079:
7077:
7074:
7072:
7069:
7067:
7064:
7062:
7059:
7057:
7054:
7052:
7049:
7047:
7044:
7042:
7039:
7037:
7034:
7032:
7029:
7027:
7024:
7022:
7019:
7017:
7014:
7012:
7009:
7007:
7004:
7002:
6999:
6997:
6994:
6992:
6989:
6987:
6984:
6982:
6979:
6977:
6974:
6972:
6969:
6967:
6964:
6962:
6959:
6957:
6954:
6952:
6949:
6947:
6944:
6942:
6939:
6937:
6934:
6932:
6929:
6927:
6924:
6922:
6919:
6917:
6914:
6912:
6909:
6907:
6904:
6902:
6899:
6897:
6894:
6892:
6889:
6887:
6884:
6882:
6879:
6877:
6874:
6872:
6869:
6867:
6864:
6862:
6859:
6857:
6854:
6852:
6849:
6847:
6844:
6842:
6839:
6837:
6834:
6832:
6829:
6827:
6824:
6822:
6819:
6817:
6814:
6812:
6809:
6807:
6804:
6802:
6799:
6797:
6794:
6792:
6789:
6787:
6784:
6781:
6780:
6777:
6771:
6768:
6766:
6763:
6761:
6758:
6756:
6753:
6750:
6749:
6746:
6740:
6737:
6735:
6732:
6730:
6727:
6725:
6722:
6719:
6718:
6715:
6709:
6706:
6704:
6701:
6699:
6696:
6694:
6691:
6689:
6686:
6684:
6681:
6679:
6676:
6675:Aminoindanes:
6673:
6672:
6669:
6666:
6661:
6655:
6645:
6642:
6639:
6635:
6632:
6630:
6627:
6625:
6622:
6620:
6617:
6615:
6614:Isometheptene
6612:
6610:
6607:
6605:
6604:Hexacyclonate
6602:
6600:
6597:
6595:
6592:
6590:
6587:
6585:
6582:
6580:
6577:
6575:
6572:
6570:
6567:
6565:
6562:
6560:
6557:
6555:
6552:
6550:
6547:
6545:
6542:
6540:
6537:
6534:
6533:
6530:
6524:
6521:
6519:
6516:
6514:
6511:
6509:
6506:
6504:
6501:
6499:
6496:
6494:
6491:
6489:
6486:
6483:
6482:
6479:
6473:
6470:
6468:
6467:Xylopropamine
6465:
6463:
6460:
6458:
6455:
6452:
6445:
6442:
6440:
6437:
6435:
6432:
6430:
6427:
6425:
6423:
6419:
6417:
6414:
6412:
6409:
6407:
6404:
6402:
6399:
6397:
6394:
6392:
6389:
6387:
6385:
6381:
6379:
6377:
6373:
6371:
6368:
6366:
6363:
6361:
6358:
6356:
6353:
6351:
6348:
6346:
6345:Methcathinone
6343:
6339:
6336:
6334:
6331:
6330:
6329:
6326:
6324:
6323:Mephentermine
6321:
6319:
6316:
6314:
6311:
6309:
6306:
6304:
6301:
6299:
6296:
6294:
6291:
6289:
6286:
6284:
6281:
6279:
6276:
6274:
6271:
6269:
6266:
6264:
6261:
6259:
6256:
6253:
6250:
6248:
6245:
6243:
6240:
6238:
6235:
6233:
6230:
6228:
6225:
6223:
6220:
6218:
6215:
6213:
6210:
6208:
6205:
6203:
6200:
6198:
6195:
6193:
6190:
6188:
6185:
6183:
6180:
6178:
6175:
6173:
6170:
6168:
6165:
6163:
6160:
6158:
6155:
6153:
6150:
6148:
6145:
6143:
6140:
6138:
6135:
6133:
6132:Benzphetamine
6130:
6128:
6125:
6123:
6120:
6118:
6115:
6111:
6108:
6106:
6103:
6102:
6101:
6098:
6096:
6093:
6091:
6088:
6086:
6083:
6081:
6078:
6076:
6073:
6071:
6068:
6066:
6063:
6061:
6058:
6056:
6053:
6051:
6048:
6045:
6044:
6041:
6035:
6032:
6030:
6027:
6025:
6022:
6020:
6017:
6015:
6012:
6010:
6007:
6005:
6002:
6000:
5997:
5994:
5993:
5990:
5984:
5981:
5979:
5978:Phenmetrazine
5976:
5974:
5971:
5969:
5966:
5964:
5961:
5959:
5956:
5954:
5951:
5948:
5947:
5944:
5941:
5936:
5930:
5918:
5915:
5914:
5913:
5910:
5908:
5905:
5903:
5900:
5898:
5895:
5893:
5890:
5888:
5885:
5883:
5882:Isometheptene
5880:
5878:
5875:
5873:
5872:Hexacyclonate
5870:
5868:
5865:
5863:
5860:
5858:
5855:
5853:
5850:
5848:
5845:
5843:
5840:
5838:
5835:
5833:
5830:
5828:
5825:
5823:
5820:
5818:
5815:
5813:
5810:
5808:
5805:
5803:
5800:
5797:
5796:
5793:
5787:
5784:
5782:
5779:
5777:
5774:
5772:
5769:
5767:
5764:
5762:
5759:
5756:
5755:
5752:
5746:
5743:
5741:
5740:Xylopropamine
5738:
5736:
5733:
5731:
5728:
5726:
5723:
5721:
5718:
5716:
5713:
5711:
5708:
5706:
5703:
5701:
5698:
5696:
5693:
5691:
5689:
5685:
5683:
5681:
5677:
5675:
5673:
5669:
5667:
5664:
5662:
5659:
5657:
5654:
5652:
5649:
5647:
5644:
5642:
5639:
5637:
5634:
5632:
5629:
5627:
5624:
5622:
5619:
5617:
5614:
5612:
5609:
5607:
5604:
5602:
5601:Methcathinone
5599:
5595:
5592:
5590:
5587:
5586:
5585:
5582:
5580:
5577:
5575:
5572:
5570:
5567:
5565:
5562:
5560:
5557:
5555:
5552:
5550:
5547:
5545:
5542:
5540:
5537:
5535:
5532:
5530:
5527:
5525:
5522:
5520:
5517:
5515:
5512:
5510:
5507:
5505:
5502:
5500:
5497:
5495:
5492:
5490:
5487:
5485:
5482:
5480:
5477:
5475:
5472:
5470:
5467:
5465:
5462:
5460:
5457:
5455:
5452:
5450:
5447:
5445:
5442:
5440:
5437:
5435:
5434:Benzphetamine
5432:
5430:
5427:
5425:
5422:
5420:
5417:
5415:
5412:
5409:
5406:
5404:
5400:
5397:
5395:
5392:
5390:
5387:
5385:
5382:
5380:
5377:
5375:
5372:
5370:
5367:
5365:
5362:
5360:
5357:
5355:
5352:
5350:
5347:
5344:
5343:
5340:
5334:
5331:
5329:
5326:
5324:
5321:
5319:
5316:
5314:
5311:
5309:
5306:
5304:
5301:
5299:
5296:
5293:
5292:
5289:
5283:
5280:
5278:
5277:Phenmetrazine
5275:
5273:
5270:
5268:
5265:
5263:
5260:
5258:
5255:
5253:
5250:
5247:
5246:
5243:
5240:
5235:
5229:
5225:
5218:
5213:
5211:
5206:
5204:
5199:
5198:
5195:
5185:
5181:
5176:
5170:
5167:
5165:
5162:
5160:
5157:
5155:
5152:
5150:
5149:Thiopropamine
5147:
5145:
5142:
5140:
5137:
5135:
5132:
5130:
5127:
5125:
5122:
5120:
5117:
5115:
5112:
5110:
5107:
5105:
5102:
5100:
5097:
5095:
5092:
5090:
5087:
5085:
5082:
5080:
5077:
5075:
5072:
5070:
5067:
5065:
5062:
5060:
5057:
5055:
5052:
5050:
5049:Meclofenoxate
5047:
5045:
5042:
5040:
5037:
5035:
5032:
5030:
5027:
5025:
5022:
5020:
5017:
5015:
5012:
5010:
5007:
5005:
5002:
5000:
4999:Hexacyclonate
4997:
4995:
4992:
4990:
4987:
4985:
4982:
4980:
4977:
4975:
4972:
4970:
4967:
4965:
4962:
4960:
4957:
4955:
4952:
4950:
4947:
4945:
4942:
4940:
4937:
4935:
4932:
4930:
4927:
4925:
4922:
4920:
4917:
4915:
4914:Centanafadine
4912:
4910:
4907:
4905:
4902:
4900:
4897:
4895:
4892:
4890:
4887:
4885:
4882:
4880:
4877:
4875:
4872:
4870:
4867:
4865:
4862:
4860:
4857:
4856:
4854:
4850:
4844:
4841:
4839:
4836:
4834:
4831:
4829:
4826:
4824:
4821:
4819:
4816:
4814:
4811:
4809:
4806:
4804:
4801:
4799:
4796:
4794:
4791:
4789:
4786:
4785:
4783:
4781:
4777:
4771:
4768:
4766:
4763:
4761:
4758:
4756:
4753:
4751:
4748:
4746:
4743:
4741:
4738:
4736:
4733:
4731:
4728:
4726:
4723:
4721:
4718:
4716:
4713:
4711:
4708:
4706:
4703:
4701:
4698:
4696:
4693:
4691:
4688:
4686:
4683:
4681:
4678:
4676:
4673:
4671:
4668:
4666:
4663:
4661:
4658:
4656:
4653:
4651:
4650:Ioflupane (I)
4648:
4646:
4643:
4641:
4638:
4636:
4633:
4631:
4628:
4626:
4623:
4621:
4618:
4616:
4613:
4611:
4608:
4606:
4603:
4601:
4598:
4596:
4593:
4591:
4588:
4587:
4585:
4583:
4579:
4573:
4570:
4568:
4565:
4563:
4560:
4559:
4557:
4555:
4551:
4545:
4542:
4540:
4537:
4535:
4532:
4530:
4527:
4525:
4522:
4520:
4517:
4515:
4512:
4510:
4507:
4505:
4502:
4500:
4497:
4495:
4492:
4490:
4487:
4485:
4482:
4480:
4477:
4475:
4472:
4470:
4467:
4465:
4462:
4460:
4457:
4455:
4452:
4450:
4447:
4445:
4442:
4440:
4437:
4435:
4432:
4430:
4427:
4425:
4422:
4420:
4417:
4415:
4412:
4410:
4407:
4405:
4402:
4401:
4399:
4397:
4393:
4387:
4384:
4382:
4379:
4377:
4374:
4372:
4369:
4367:
4366:Phacetoperane
4364:
4362:
4359:
4356:
4352:
4349:
4347:
4344:
4342:
4339:
4337:
4334:
4332:
4329:
4327:
4324:
4322:
4319:
4317:
4314:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4277:
4274:
4273:
4271:
4269:
4265:
4259:
4256:
4254:
4251:
4249:
4246:
4244:
4241:
4239:
4236:
4234:
4231:
4229:
4226:
4224:
4221:
4219:
4216:
4214:
4211:
4209:
4206:
4204:
4201:
4199:
4196:
4194:
4191:
4190:
4188:
4186:
4182:
4176:
4173:
4171:
4168:
4166:
4163:
4161:
4160:Phenmetrazine
4158:
4156:
4153:
4151:
4148:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4128:
4126:
4123:
4121:
4118:
4116:
4113:
4111:
4108:
4107:
4105:
4103:
4099:
4093:
4090:
4088:
4087:Xylopropamine
4085:
4083:
4080:
4078:
4075:
4073:
4070:
4068:
4065:
4063:
4062:Theodrenaline
4060:
4058:
4055:
4053:
4050:
4048:
4045:
4042:
4038:
4035:
4033:
4030:
4028:
4025:
4023:
4020:
4018:
4015:
4013:
4010:
4008:
4005:
4003:
4000:
3998:
3995:
3993:
3990:
3988:
3985:
3983:
3980:
3978:
3977:Phenylephrine
3975:
3973:
3972:Phenylalanine
3970:
3968:
3965:
3963:
3960:
3958:
3955:
3953:
3950:
3948:
3945:
3943:
3940:
3938:
3935:
3933:
3930:
3928:
3925:
3923:
3920:
3918:
3915:
3913:
3912:Orciprenaline
3910:
3908:
3905:
3903:
3897:
3895:
3892:
3890:
3887:
3885:
3882:
3880:
3877:
3875:
3872:
3870:
3867:
3865:
3862:
3860:
3857:
3855:
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3835:
3832:
3830:
3827:
3825:
3822:
3820:
3817:
3814:
3810:
3806:
3803:
3801:
3798:
3796:
3793:
3791:
3788:
3786:
3785:Mephentermine
3783:
3781:
3778:
3776:
3773:
3771:
3768:
3766:
3763:
3761:
3758:
3756:
3753:
3751:
3748:
3746:
3743:
3741:
3738:
3736:
3733:
3731:
3728:
3726:
3723:
3721:
3718:
3715:
3709:
3707:
3704:
3702:
3699:
3697:
3694:
3692:
3689:
3687:
3684:
3682:
3679:
3677:
3674:
3672:
3669:
3667:
3664:
3662:
3659:
3657:
3654:
3652:
3649:
3647:
3644:
3642:
3639:
3637:
3634:
3632:
3629:
3626:
3622:
3618:
3615:
3613:
3610:
3608:
3605:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3585:
3583:
3580:
3578:
3575:
3573:
3570:
3568:
3565:
3563:
3560:
3558:
3555:
3553:
3550:
3548:
3545:
3543:
3540:
3537:
3533:
3529:
3526:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3498:
3496:
3493:
3491:
3488:
3486:
3483:
3481:
3478:
3476:
3473:
3471:
3468:
3466:
3463:
3461:
3458:
3456:
3453:
3451:
3448:
3446:
3443:
3441:
3438:
3436:
3433:
3431:
3428:
3426:
3425:Benzphetamine
3423:
3421:
3418:
3416:
3413:
3411:
3408:
3406:
3403:
3401:
3398:
3395:
3391:
3387:
3384:
3382:
3379:
3377:
3374:
3372:
3369:
3367:
3366:2-Aminoindane
3364:
3362:
3359:
3357:
3354:
3352:
3349:
3347:
3344:
3342:
3339:
3337:
3334:
3332:
3329:
3327:
3324:
3322:
3319:
3317:
3314:
3312:
3309:
3307:
3304:
3302:
3299:
3297:
3294:
3292:
3289:
3287:
3284:
3282:
3279:
3277:
3274:
3272:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3252:
3249:
3247:
3244:
3243:
3241:
3239:
3235:
3229:
3226:
3224:
3221:
3219:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3199:
3196:
3194:
3191:
3190:
3188:
3186:
3182:
3176:
3173:
3171:
3168:
3166:
3163:
3161:
3158:
3156:
3153:
3151:
3148:
3147:
3145:
3143:
3139:
3133:
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3093:
3090:
3089:
3087:
3085:
3081:
3075:
3072:
3070:
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
3000:
2997:
2995:
2992:
2990:
2987:
2985:
2982:
2980:
2977:
2975:
2972:
2970:
2967:
2965:
2962:
2960:
2957:
2955:
2952:
2950:
2947:
2945:
2942:
2940:
2937:
2935:
2932:
2930:
2927:
2925:
2922:
2920:
2917:
2916:
2914:
2912:
2908:
2902:
2899:
2897:
2894:
2892:
2889:
2887:
2884:
2882:
2879:
2877:
2874:
2872:
2869:
2867:
2864:
2862:
2859:
2857:
2856:Methcathinone
2854:
2852:
2849:
2847:
2844:
2842:
2839:
2837:
2834:
2832:
2829:
2827:
2824:
2822:
2819:
2817:
2814:
2812:
2809:
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2698:
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2695:Tenocyclidine
2693:
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2690:Rolicyclidine
2688:
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2685:Phencyclidine
2683:
2681:
2680:Phencyclamine
2678:
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2524:Isometheptene
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2446:Aminophylline
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2011:
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1975:Globalnews.ca
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1520:
1516:
1513:
1509:
1505:
1501:
1500:methcathinone
1495:
1493:
1489:
1485:
1484:primary amine
1481:
1480:propiophenone
1477:
1473:
1472:
1462:
1455:
1453:
1451:
1447:
1443:
1439:
1431:
1427:
1424:
1419:
1418:propiophenone
1415:
1399:
1392:
1380:
1368:
1366:
1364:
1360:
1356:
1350:
1344:
1340:
1336:
1332:
1328:
1327:cinnamic acid
1324:
1323:phenylalanine
1315:
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1303:
1301:
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1221:
1219:
1217:
1213:
1209:
1205:
1204:buccal mucosa
1196:
1194:
1192:
1191:smooth muscle
1188:
1180:
1175:
1173:
1167:
1165:
1161:
1157:
1153:
1149:
1145:
1141:
1140:aromatic ring
1137:
1133:
1130:(CNS). These
1129:
1125:
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1051:United States
1050:
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830:
826:
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808:
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802:
798:
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790:
786:
777:
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768:
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760:
757:
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749:
744:
740:
736:
732:
728:
721:
716:
714:
712:
709:
705:
701:
697:
696:methcathinone
693:
690:
686:
682:
678:
674:
670:
669:methcathinone
666:
662:
658:
654:
653:
649:
646:found in the
645:
642:
638:
634:
628:
595:
585:
578:
572:
563:
558:
554:
547:
538:
534:
527:
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513:
510:
505:
498:
496:
492:
471:
469:
465:
460:
456:
452:
449:
447:
445:ECHA InfoCard
441:
433:
429:
428:DTXSID0050427
425:
424:
422:
413:
409:
402:
401:ChEMBL2104047
398:
397:
395:
393:
389:
382:
378:
377:
375:
373:
369:
362:
358:
357:
355:
353:
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342:
338:
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335:
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329:
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318:
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309:
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297:
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289:
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278:
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264:
257:
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236:
232:
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221:
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203:
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195:
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179:
177:
167:
165:
155:
152:
143:
141:
132:
129:
119:
116:
106:
105:
103:
101:
97:
92:
85:
84:
82:
80:
76:
72:
71:Psychological
68:
65:
63:
57:
54:Clinical data
52:
48:
43:
39:
34:
24:
19:
9456:Solriamfetol
9371:Famprofazone
9277:
9269:
9255:-Octopamine)
9252:
9249:Norfenefrine
9204:Metanephrine
9196:
9152:Isoprenaline
9108:(Dextrodopa)
9093:Adrenochrome
9051:Pyrovalerone
8957:
8936:
8895:Entactogens:
8894:
8844:Entactogens:
8843:
8790:Ethcathinone
8779:
8706:
8685:
8674:Entactogens:
8673:
8636:
8629:Phentermines
8592:
8441:Entactogens:
8440:
8437:Zylofuramine
8215:Fenfluramine
8210:Fenethylline
8160:Amphetaminil
8141:Amfepentorex
8102:
7960:
7953:Amphetamines
7934:
7918:Entactogens:
7917:
7903:
7895:
7887:
7879:
7843:
7841:
7817:Metaescaline
7419:
7334:
7333:
7317:Guanethidine
7293:
7283:
7271:
7268:
7244:Indeloxazine
7240:
7188:4-Methyl-αMT
7183:4-Methyl-αET
7180:Tryptamines:
7179:
7099:Piperazines:
7098:
6931:Fenfluramine
6831:6-Methyl-MDA
6821:5-Methyl-MDA
6786:2-Methyl-MDA
6782:
6751:
6720:
6674:
6589:Feprosidnine
6569:Clofenciclan
6535:
6485:Piperazines:
6484:
6472:Zylofuramine
6421:
6383:
6375:
6217:Fenethylline
6212:Famprofazone
6197:Ethcathinone
6156:
6117:Amphetaminil
6090:Amfepentorex
6046:
5995:
5958:Fenmetramide
5953:Fenbutrazate
5950:Morpholines:
5949:
5857:Feprosidnine
5837:Clofenciclan
5798:
5758:Piperazines:
5757:
5745:Zylofuramine
5687:
5679:
5671:
5519:Fenethylline
5514:Famprofazone
5494:Ethcathinone
5453:
5414:Amphetaminil
5389:Amfepentorex
5345:
5294:
5257:Fenmetramide
5252:Fenbutrazate
5249:Morpholines:
5248:
5104:Oxaprotiline
5054:Medifoxamine
4974:Fenpentadiol
4954:Dimethocaine
4949:Diclofensine
4929:Cropropamide
4924:Clofenciclan
4879:Amiphenazole
4833:7-Methyl-αET
4828:6-Fluoro-αMT
4808:5-Fluoro-αMT
4803:5-Chloro-αMT
4798:4-Methyl-αMT
4793:4-Methyl-αET
4635:Difluoropine
4620:Cocaethylene
4605:Brasofensine
4544:Pyrovalerone
4396:Pyrrolidines
4120:Fenmetramide
4115:Fenbutrazate
4092:Zylofuramine
4052:Solriamfetol
3884:Norfenefrine
3790:Metanephrine
3716:(Selegiline)
3706:Isoprenaline
3636:Feprosidnine
3617:Fenfluramine
3612:Fenethylline
3597:Famprofazone
3470:Cinnamedrine
3400:Amphetaminil
3351:Amfepentorex
3029:Sazetidine A
2994:Ispronicline
2959:Bradanicline
2911:Cholinergics
2826:Ethcathinone
2815:
2710:Benzazepines
2665:Eticyclidine
2486:Theophylline
2471:Paraxanthine
2308:. Retrieved
2299:
2277:10 September
2275:. Retrieved
2266:
2256:
2221:
2217:
2184:. Retrieved
2175:
2130:
2126:
2120:
2108:. Retrieved
2099:
2069:. Retrieved
2057:
2044:
2035:
2026:
2014:. Retrieved
2005:
1995:
1983:. Retrieved
1979:the original
1974:
1964:
1952:. Retrieved
1948:the original
1944:The Guardian
1943:
1933:
1921:. Retrieved
1917:the original
1907:
1896:the original
1891:
1879:
1846:
1842:
1805:. Retrieved
1796:
1786:
1753:
1749:
1701:
1697:
1647:
1643:
1633:
1622:. Retrieved
1600:
1590:
1542:
1531:
1518:
1496:
1475:
1471:Catha edulis
1469:
1467:
1411:
1397:
1363:benzaldehyde
1351:
1335:benzoic acid
1320:
1309:Biosynthesis
1266:constipation
1263:
1243:irritability
1233:
1225:
1200:
1197:Pharmacology
1176:
1168:
1109:
939:Saudi Arabia
907:South Africa
852:
837:
818:
809:
805:
782:
761:
725:
681:Catha edulis
680:
673:amphetamines
652:Catha edulis
650:
636:
632:
593:
592:
581:
575:
234:
206:Elimination
140:Schedule III
100:Legal status
94:Legal status
18:
9517:Euphoriants
9476:Venlafaxine
9441:Pronethalol
9411:Methoxamine
9341:Dizocilpine
9336:Diphenidine
9311:Amidephrine
9272:-Octopamine
9209:Metaraminol
9176:(Droxidopa)
9122:Epinephrine
9112:Dimetofrine
8958:Stimulants:
8937:Stimulants:
8765:Brephedrone
8755:Amfepramone
8707:Stimulants:
8689:Cericlamine
8670:Phentermine
8650:Clortermine
8637:Stimulants:
8417:Sibutramine
8402:Prenylamine
8337:Oxifentorex
8289:Metaraminol
8229:Fenproporex
8200:Fencamfamin
8180:Clobenzorex
8146:Amphetamine
8103:Stimulants:
7844:Stimulants:
7802:Macromerine
7346:Adrenergics
7312:Guanazodine
7297:Bethanidine
7142:Mepiprazole
6936:Flephedrone
6876:Amfepramone
6856:Brephedrone
6752:Oxazolines:
6584:Cyprodenate
6429:Prenylamine
6411:Phentermine
6227:Flephedrone
6222:Fenproporex
6167:Clortermine
6162:Clobenzorex
6100:Amphetamine
6095:Amfepramone
6034:Thozalinone
6014:Cyclazodone
5996:Oxazolines:
5852:Cyprodenate
5715:Prenylamine
5529:Flephedrone
5524:Fenproporex
5464:Clortermine
5459:Clobenzorex
5399:Amphetamine
5394:Amfepramone
5333:Thozalinone
5313:Cyclazodone
5295:Oxazolines:
5154:Thiothinone
5139:Tametraline
5124:Rauwolscine
5094:Nomifensine
5089:Nikethamide
5034:Lomevactone
5019:JNJ-7925476
5014:Indatraline
4989:GSK1360707F
4944:Desipramine
4934:Crotetamide
4919:Ciclazindol
4899:Benzydamine
4889:Atomoxetine
4884:Atipamezole
4780:Tryptamines
4750:Tesofensine
4316:Difemetorex
4268:Piperidines
4185:Piperazines
4047:Sibutramine
4017:Prenylamine
3967:Phentermine
3922:Oxifentorex
3819:Methoxamine
3795:Metaraminol
3631:Fenproporex
3602:Fencamfamin
3567:Epinephrine
3490:Clortermine
3480:Clobenzorex
3475:Clenbuterol
3450:Camfetamine
3386:Amphetamine
3356:Amidephrine
3228:Thozalinone
3208:Cyclazodone
3155:Armodafinil
3117:Pentetrazol
3097:Bicuculline
3084:Convulsants
3074:WAY-317,538
3069:Varenicline
3059:Tebanicline
3039:SSR-180,711
3024:Rivanicline
3019:Pozanicline
3014:PNU-282,987
3009:PNU-120,596
3004:PHA-543,613
2984:Epiboxidine
2979:Epibatidine
2944:Altinicline
2836:Flephedrone
2791:Amfepramone
2670:Gacyclidine
2514:Cyprodenate
2496:Alkylamines
2481:Theobromine
2413:Rimantadine
2385:Adamantanes
2172:"Cathinone"
2000:Extance A.
1504:amphetamine
1331:benzoyl-CoA
1294:hot flashes
1278:oral cancer
1274:gum disease
1231:frequency.
1148:hydrophobic
1116:epinephrine
1067:New Zealand
1027:Switzerland
995:Netherlands
862:Regulation
789:East Africa
502: g·mol
451:100.163.927
218:Identifiers
9527:Stimulants
9502:Cathinones
9491:Categories
9446:Salbutamol
9381:Hexapradol
9361:Etafedrine
9356:Ephenidine
9351:Dopexamine
9346:Dobutamine
9326:Denopamine
9316:Arbutamine
9290:Synephrine
9224:Methyldopa
9219:Metirosine
9167:(Levodopa)
9157:Isoetarine
9142:Fenclonine
9132:Etilefrine
9046:Prolintane
8877:Mephedrone
8840:Radafaxine
8830:Pentedrone
8810:Methedrone
8770:Buphedrone
8760:Benzedrone
8699:Cathinones
8611:Selegiline
8601:Amiflamine
8397:Pholedrine
8347:Ortetamine
8342:Oxilofrine
8274:Lefetamine
8264:Iofetamine
8249:Furfenorex
8244:Formetorex
8234:Flucetorex
8165:Benfluorex
8136:Amfecloral
8131:Alfetamine
8004:D-Deprenyl
7921:Lophophine
7832:Psi-2C-T-4
7827:Proscaline
7797:Jimscaline
7287:SoRI-20041
7280:SoRI-20040
7228:Tryptamine
7011:Methedrone
7006:Mephedrone
6961:Lophophine
6951:Iofetamine
6941:Flucetorex
6841:Amiflamine
6770:Fluminorex
6765:Clominorex
6599:Heptaminol
6594:Gilutensin
6579:Cypenamine
6444:Selegiline
6401:Pholedrine
6370:Ortetamine
6350:Methedrone
6318:Mephedrone
6268:Lophophine
6237:Furfenorex
6142:Buphedrone
6085:Amfecloral
6080:Alfetamine
6024:Fluminorex
6019:Fenozolone
6009:Clominorex
5867:Heptaminol
5862:Gilutensin
5847:Cypenamine
5832:Amineptine
5705:Pholedrine
5695:Pholedrine
5666:Ortetamine
5606:Methedrone
5574:Mephedrone
5564:Lophophine
5539:Furfenorex
5469:D-Deprenyl
5439:Buphedrone
5384:Amfecloral
5379:Alfetamine
5323:Fluminorex
5318:Fenozolone
5308:Clominorex
5134:Setazindol
5119:Rasagiline
5109:PNU-99,194
5059:Mefexamide
5029:Leptacline
5024:Lazabemide
4994:GYKI-52895
4984:Gilutensin
4909:BTS 74,398
4874:Amineptine
4823:5-MeO-DIPT
4655:Norcocaine
4645:FP-β-CPPIT
4640:FE-β-CPPIT
4562:Oxiracetam
4539:Prolintane
4258:Vanoxerine
4175:Radafaxine
4150:PD-128,907
4145:Oxaflozane
4130:Manifaxine
4057:Synephrine
4037:Salbutamol
4032:Ropinirole
3987:Pholedrine
3927:Oxilofrine
3917:Ortetamine
3907:Octopamine
3874:Nisoxetine
3730:Lophophine
3720:Lefetamine
3701:Isoetarine
3696:Iofetamine
3661:Hexapradol
3651:Furfenorex
3646:Formetorex
3592:Etilefrine
3577:Etafedrine
3547:Dopexamine
3532:Dextrodopa
3523:Dobutamine
3508:Denopamine
3495:Cypenamine
3465:Cilobamine
3420:Benfluorex
3405:Arbutamine
3346:Amfecloral
3336:Alfetamine
3218:Fluminorex
3213:Fenozolone
3203:Clominorex
3185:Oxazolines
3165:CRL-40,941
3160:CRL-40,940
3127:Strychnine
3122:Picrotoxin
3092:Anatoxin-a
2974:Dianicline
2891:Pentedrone
2861:Methedrone
2851:Mephedrone
2801:Buphedrone
2796:Benzedrone
2743:Cathinones
2700:Tiletamine
2660:Esketamine
2602:LY-503,430
2597:LY-404,187
2519:Heptaminol
2509:Cypenamine
2461:Dimethazan
2403:Bromantane
2398:Amantadine
2393:Adapromine
2377:Stimulants
2302:. EMCDDA.
2100:slideshare
2071:2017-08-26
1923:7 December
1624:2023-08-27
1582:References
1426:amino acid
1355:Coenzyme A
1286:depression
1250:Depression
1136:monoamines
848:bath salts
821:Schedule I
756:Madagascar
704:mephedrone
679:effect of
671:and other
507:3D model (
495:Molar mass
381:CHEBI:4110
341:540EI4406J
312:ChemSpider
256:71031-15-7
247:CAS Number
227:IUPAC name
176:Schedule I
69:: no data
60:Dependence
9426:PARGY-LAD
9321:Cafedrine
9280:-Tyramine
9234:Nordefrin
9214:Metaterol
9199:-Tyramine
9191:-Tyrosine
9147:Ibopamine
9036:Naphyrone
8867:Methylone
8835:Pentylone
8780:Cathinone
8775:Bupropion
8618:-Deprenyl
8284:Mefenorex
8254:Gepefrine
8205:Fencamine
8190:Ephedrine
8126:Acridorex
7853:Hordenine
7812:Mescaline
7705:2C-T-22.5
7443:25N-NBOMe
7438:25I-NBOMe
7433:25D-NBOMe
7428:25C-NBOMe
7423:25B-NBOMe
7335:See also:
7307:Guanadrel
7302:Bretylium
7275:SoRI-9804
7249:Viqualine
7203:5-MeO-αMT
7198:5-MeO-αET
7016:Methylone
6729:8-OH-DPAT
6624:Octodrine
6609:Indanorex
6451:-Deprenyl
6355:Methylone
6313:Mefenorex
6242:Hordenine
6192:Ephedrine
6157:Cathinone
5897:Octodrine
5877:Indanorex
5656:Methylone
5569:Mefenorex
5544:Hordenine
5489:Ephedrine
5454:Cathinone
5169:Yohimbine
5144:Tandamine
5114:PRC200-SS
5009:Indanorex
4979:Gamfexine
4969:Fenisorex
4894:Bemegride
4818:5-MeO-αMT
4813:5-MeO-αET
4760:Tropoxane
4534:Picilorex
4524:Naphyrone
4371:Pipradrol
4238:GBR-13119
4233:GBR-13098
4228:GBR-13069
4223:GBR-12935
4218:GBR-12783
3957:Phenatine
3780:Mefenorex
3714:-Deprenyl
3686:Ibopamine
3671:Hordenine
3656:Gepefrine
3607:Fencamine
3562:Ephedrine
3552:Droxidopa
3503:-Deprenyl
3381:Acridorex
3175:Modafinil
3170:Fluorenol
3150:Adrafinil
3142:Eugeroics
3107:Flurothyl
3034:SIB-1553A
2954:Arecoline
2949:Anabasine
2939:AR-R17779
2924:A-366,833
2896:Pentylone
2876:Mexedrone
2871:Methylone
2841:Hexedrone
2816:Cathinone
2806:Bupropion
2733:SKF-82958
2728:SKF-81297
2723:SKF-77434
2627:Sunifiram
2612:Org 26576
2607:Nooglutyl
2559:Ampakines
2539:Octodrine
2476:SCH-58261
2456:CGS-15943
2408:Memantine
2176:Drug Bank
1561:Bupropion
1545:methylone
1534:Bupropion
1456:Structure
1359:hydration
1304:Chemistry
1270:heartburn
1124:serotonin
1086:Illegal
1059:Australia
722:Discovery
711:bupropion
677:stimulant
661:ephedrine
641:monoamine
594:Cathinone
213:0.7–2.3 h
208:half-life
62:liability
30:Cathinone
9431:Phenibut
9117:Dopamine
9098:Ciladopa
9088:a-Me-TRA
8928:Eutylone
8918:Butylone
8862:Ethylone
8857:Butylone
8847:3,4-DMMC
8795:Eutylone
8745:4-MeMABP
8665:Pentorex
8655:Etolorex
8645:Cloforex
8422:Tiflorex
8314:Morforex
8239:Fludorex
7994:Beatrice
7787:Escaline
7322:Guanoxan
7102:2C-B-BZP
6926:Etolorex
6921:Ethylone
6871:Cloforex
6861:Butylone
6760:Aminorex
6488:2C-B-BZP
6462:Tyramine
6457:Tiflorex
6391:Pentorex
6360:Morforex
6232:Fludorex
6202:Ethylone
6147:Butylone
6122:β-Me-PEA
6050:2-OH-PEA
6029:Pemoline
6004:Aminorex
5968:Morforex
5963:Morazone
5761:2C-B-BZP
5735:Tyramine
5730:Tiflorex
5661:Morforex
5534:Fludorex
5504:Ethylone
5444:Butylone
5419:β-Me-PEA
5349:2-OH-PEA
5328:Pemoline
5303:Aminorex
5267:Morforex
5262:Morazone
5180:ATC code
5044:Mazindol
5004:Idazoxan
4964:Etamivan
4959:Efaroxan
4788:4-HO-αMT
4582:Tropanes
4554:Racetams
4409:4-Cl-PVP
4386:SCH-5472
4346:JZ-IV-10
4193:2C-B-BZP
4140:Morforex
4135:Morazone
4082:Tyrosine
4077:Tyramine
4067:Tiflorex
3952:Pentorex
3854:Morforex
3800:Mesocarb
3641:Fludorex
3542:Dopamine
3536:Levodopa
3485:Cloforex
3266:2-OH-PEA
3223:Pemoline
3198:Aminorex
3112:Gabazine
2999:Nicotine
2969:Cytisine
2964:Cotinine
2919:A-84,543
2831:Ethylone
2811:Butylone
2756:3,4-DMMC
2718:6-Br-APB
2675:Ketamine
2632:Unifiram
2451:Caffeine
2332:Archived
2304:Archived
2271:Archived
2248:22215969
2186:10 March
2180:Archived
2155:20621923
2104:Archived
2062:Archived
2016:3 August
2010:Archived
1985:19 April
1954:19 April
1863:12203257
1807:20 March
1801:Archived
1797:BBC News
1778:25788465
1720:12858935
1674:12848785
1618:Archived
1595:5903121.
1555:See also
1492:dimerize
1343:pyruvate
1298:lethargy
1259:insomnia
1164:dopamine
1158:between
1112:dopamine
1091:Bulgaria
1070:Illegal
1062:Illegal
1054:Illegal
1038:Illegal
1030:Illegal
1022:Illegal
1014:Illegal
1006:Illegal
966:Illegal
958:Illegal
942:Illegal
934:Illegal
931:Malaysia
918:Illegal
891:Djibouti
875:Ethiopia
815:Legality
801:caffeine
797:Djibouti
793:Ethiopia
739:euphoric
706:and the
644:alkaloid
584:(verify)
292:DrugBank
151:Anlage I
128:Class F2
79:ATC code
67:Physical
9471:UWA-101
9436:PRO-LAD
9366:ETH-LAD
9127:Epinine
9083:a-Me-DA
9006:4-MePPP
9001:4-MePHP
8996:4-MePBP
8908:Ariadne
8686:Others:
8596:3,4-DCA
8593:Others:
8544:2,3-MDA
8529:6-MAPDB
8494:5-MAPDB
8175:Cathine
8099:ZDCM-04
8084:Psi-DOM
8069:Ganesha
7935:Others:
7750:2C-T-33
7745:2C-T-32
7740:2C-T-31
7735:2C-T-30
7730:2C-T-28
7725:2C-T-27
7720:2C-T-25
7715:2C-T-24
7710:2C-T-23
7700:2C-T-22
7695:2C-T-21
7690:2C-T-20
7685:2C-T-19
7680:2C-T-18
7675:2C-T-17
7670:2C-T-16
7665:2C-T-15
7660:2C-T-14
7655:2C-T-13
7650:2C-T-12
7645:2C-T-11
7640:2C-T-10
7455:2C-B-AN
7241:Others:
7107:3-MeOPP
6536:Others:
6152:Cathine
5799:Others:
5449:Cathine
5159:Trazium
5084:Nefopam
5039:LR-5182
4740:RTI-386
4735:RTI-371
4730:RTI-354
4725:RTI-336
4720:RTI-229
4715:RTI-177
4710:RTI-150
4705:RTI-126
4695:RTI-120
4690:RTI-113
4685:RTI-112
4625:Cocaine
4414:5-DBFPV
4361:Nocaine
4213:DBL-583
3572:Epinine
3455:Cathine
3331:AL-1095
3276:2,3-MDA
3132:Thujone
3054:TC-2216
3049:TC-1827
3044:TC-1698
2934:ABT-418
2929:ABT-202
2622:S-18986
2592:IDRA-21
2310:8 March
2239:3229120
2147:6791236
2110:8 March
1871:9749292
1799:. BBC.
1770:7910126
1665:1884326
1523:cathine
1208:stomach
1160:neurons
1142:and an
1126:in the
1075:Georgia
987:Ireland
979:Germany
963:Finland
955:Denmark
883:Somalia
867:Eritrea
764:placebo
743:cathine
717:History
665:cathine
639:) is a
500:149.193
468:Formula
301:DB01560
267:PubChem
164:Class C
149::
138::
9386:IP-LAD
9306:AL-LAD
9078:6-OHDA
8613:(also
8606:DiFMDA
8524:6-MAPB
8514:6-EAPB
8504:6-APDB
8489:5-MAPB
8479:5-EAPB
8474:5-APDB
8079:MMDA-2
7979:3C-MAL
7931:MDMPEA
7782:DESOXY
7760:2C-TFM
7755:2C-TFE
7635:2C-T-9
7630:2C-T-8
7625:2C-T-7
7620:2C-T-6
7615:2C-T-5
7610:2C-T-4
7605:2C-T-3
7600:2C-T-2
7575:2C-O-4
7565:2C-NH2
7540:2C-G-N
7535:2C-G-6
7530:2C-G-5
7525:2C-G-4
7520:2C-G-3
7515:2C-G-2
7510:2C-G-1
7262:Others
7162:pTFMPP
7051:4-TFMA
6991:MDMPEA
6826:6-APDB
6816:5-APDB
6446:(also
6298:MDMPEA
6252:5-APDI
5822:5-APDI
5641:MDMPEA
5164:UH-232
5099:O-2172
4852:Others
4680:RTI-51
4675:RTI-32
4670:RTI-31
4444:α-PHPP
4434:α-PHiP
4429:α-PCYP
4198:3C-PEP
3760:MDMPEA
3064:UB-165
2989:GTS-21
2781:4-MEAP
2587:CX-717
2582:CX-691
2577:CX-614
2572:CX-546
2567:CX-516
2246:
2236:
2153:
2145:
1869:
1861:
1776:
1768:
1718:
1672:
1662:
1606:Anvisa
1515:oxygen
1512:ketone
1488:ketone
1486:and a
1446:acetyl
1288:. The
1216:ketone
1083:Turkey
1043:Canada
1019:Sweden
1011:Poland
1003:Norway
971:France
923:Israel
894:Legal
886:Legal
878:Legal
870:Legal
859:Region
689:ketone
533:SMILES
392:ChEMBL
361:C08301
186:
174:
162:
126:
113:
9421:MT-45
9174:-DOPS
9165:-DOPA
9106:-DOPA
9073:6-FNE
9016:MOPVP
9011:MOPPP
8986:MDPPP
8981:MDPBP
8976:α-PVP
8971:α-PPP
8966:α-PHP
8961:α-PBP
8903:4-MAB
8898:4-CAB
8852:3-MMC
8750:4-MPD
8740:4-MEC
8735:4-FMC
8730:4-EMC
8725:4-CMC
8720:4-BMC
8710:3-FMC
8682:MDMPH
8579:MMDMA
8559:MDHMA
8499:6-APB
8469:5-APB
8464:4-MTA
8459:4-MMA
8449:4-FMA
8121:3-FMA
8111:2-FMA
8064:DOTFM
8019:DMMDA
8014:DMCPA
7989:Aleph
7969:3C-BZ
7964:3C-AL
7943:DMPEA
7926:MDPEA
7837:TCB-2
7807:MEPEA
7765:2C-YN
7590:2C-SE
7585:2C-Ph
7555:2C-iP
7495:2C-EF
7480:2C-CP
7475:2C-CN
7465:2C-Bu
7460:2C-Bn
7167:TFMPP
7137:MeOPP
7132:MDBZP
7031:MMDMA
7001:MDPEA
6981:MDHMA
6896:DFMDA
6836:AEMMA
6811:4-MTA
6801:4-FMA
6791:4-CAB
6739:MDMAT
6724:6-CAT
6698:MDMAI
6678:5-IAI
6564:5-IAI
6539:2-ADN
6513:MeOPP
6508:MDBZP
6308:MDPEA
6254:(IAP)
6075:4-MMA
6065:4-FMA
6055:4-CAB
5999:4-MAR
5827:5-IAI
5802:2-ADN
5781:MeOPP
5776:MDBZP
5651:MDPEA
5616:MMDMA
5374:4-MMA
5364:4-FMA
5354:4-CAB
5298:4-MAR
4939:D-161
4859:2-MDP
4770:WF-33
4765:WF-23
4509:MOPPP
4504:MOPVP
4484:MDPBP
4479:MDPPP
4464:DMPVP
4454:α-PVT
4449:α-PVP
4439:α-PHP
4424:α-PBP
4419:α-PPP
4243:MeOPP
4208:CM156
4125:G-130
3844:MMDMA
3775:MDPEA
3326:6-FNE
3321:4-MTA
3316:4-MMA
2766:4-CMC
2761:4-BMC
2151:S2CID
2065:(PDF)
2054:(PDF)
1899:(PDF)
1888:(PDF)
1867:S2CID
1774:S2CID
1538:meta-
1187:5-HT7
1144:amine
947:Yemen
915:China
899:Kenya
752:Kenya
748:Yemen
648:shrub
635:, or
553:InChI
509:JSmol
372:ChEBI
321:56062
281:62258
9031:MPPP
9026:MPHP
9021:MPBP
8991:MDPV
8933:MBDB
8923:EBDB
8715:4-MC
8677:MDPH
8569:MDOH
8554:MDEA
8519:6-IT
8484:5-IT
8454:4-MA
8444:4-FA
8387:PMMA
8382:PMEA
8367:PFMA
8116:3-FA
8106:2-FA
8094:TeMA
8074:MMDA
8059:DOPR
8039:DOET
8034:DOEF
7984:3C-P
7974:3C-E
7770:2C-V
7595:2C-T
7580:2C-P
7570:2C-O
7560:2C-N
7550:2C-I
7545:2C-H
7505:2C-G
7500:2C-F
7490:2C-E
7485:2C-D
7470:2C-C
7450:2C-B
7208:5-MT
7193:5-CT
7157:pFPP
7152:pCPP
7147:oMPP
7127:mCPP
7122:MBZP
7117:DCPP
7081:PMMA
7076:PMEA
7036:MMMA
7026:MMDA
6996:MDOH
6976:MDEA
6966:MBDB
6916:EDMA
6911:EBDB
6906:DMMA
6806:4-HA
6796:4-FA
6734:MDAT
6703:MMAI
6693:MDAI
6688:ETAI
6683:AMMI
6659:SRAs
6559:4-BP
6554:2-BP
6549:2-AT
6544:2-AI
6523:pFPP
6518:oMPP
6503:mCPP
6498:MBZP
6303:MDOH
6283:MDEA
6273:MBDB
6187:EBDB
6182:DMMA
6070:4-MA
6060:4-FA
5934:NRAs
5817:4-BP
5812:2-AT
5807:2-AI
5786:oMPP
5771:MBZP
5646:MDOH
5631:MDEA
5621:MBDB
5611:MMDA
5499:EBDB
5479:DMMA
5369:4-MA
5359:4-FA
5233:DRAs
5184:N06B
4519:MDPV
4499:MPPP
4494:MPHP
4489:MPBP
4474:FPVP
4469:FPOP
4253:oMPP
4248:MBZP
4012:PPAP
4007:PMMA
4002:PMEA
3942:PCMA
3849:MMMA
3839:MMDA
3770:MDPR
3765:MDOH
3750:MDEA
3745:MDBU
3735:MBDB
3666:HMMA
3557:EBDB
3528:DOPA
3445:BPAP
3311:4-MA
3102:DMCM
2617:PEPA
2312:2015
2279:2013
2244:PMID
2188:2015
2143:PMID
2112:2015
2018:2018
1987:2015
1956:2015
1925:2013
1859:PMID
1809:2015
1766:PMID
1716:PMID
1670:PMID
1571:Khat
1549:MDMA
1527:khat
1432:(PCl
1284:and
1268:and
1257:and
1210:and
1122:and
787:and
754:and
733:and
727:Khat
700:MDPV
685:khat
657:khat
352:KEGG
332:UNII
200:data
86:none
9041:PEP
8913:BDB
8815:NEB
8589:TAP
8539:IAP
8534:EDA
8377:PMA
8372:PIA
8362:PFA
8357:PCA
8352:PBA
8309:MMA
8089:TMA
8054:DON
8049:DOM
8044:DOI
8029:DOC
8024:DOB
8009:DMA
7938:BOH
7223:DMT
7218:αMT
7213:αET
7112:BZP
7086:TAP
7071:PMA
7066:pIA
7061:pCA
7056:pBA
7041:NAP
7021:MMA
6946:IAP
6901:DMA
6886:DCA
6851:BOH
6846:BDB
6708:TAI
6493:BZP
6177:DMA
6137:BOH
6127:BDB
5766:BZP
5474:DMA
5429:BOH
5424:BDB
4904:BTQ
4843:αMT
4838:αET
4665:PTT
4660:PIT
4529:PEP
4203:BZP
3997:PMA
3992:PIA
3947:PHA
3937:PCA
3932:PBA
3829:MMA
3435:BOH
3430:BDB
2234:PMC
2226:doi
2135:doi
1851:doi
1758:doi
1706:doi
1660:PMC
1652:doi
1276:or
842:).
829:DEA
417:EPA
271:CID
235:(S)
9493::
8221:,
8152:,
7360:•
7356:•
7352:•
7348:•
7344:•
7340:•
7282:;
6424:IA
6386:CA
6378:BA
5690:IA
5682:CA
5674:BA
5182::
3811:,
3623:,
3534:,
3392:,
2298:.
2287:^
2269:.
2265:.
2242:.
2232:.
2222:34
2220:.
2216:.
2196:^
2178:.
2174:.
2163:^
2149:.
2141:.
2131:74
2129:.
2102:.
2098:.
2080:^
2056:.
2034:.
2008:.
2004:.
1973:.
1942:.
1890:.
1865:.
1857:.
1847:16
1845:.
1817:^
1795:.
1772:.
1764:.
1754:55
1752:.
1728:^
1714:.
1702:77
1700:.
1696:.
1682:^
1668:.
1658:.
1648:56
1646:.
1642:.
1551:.
1296:,
1280:,
1181:(α
1118:,
750:,
713:.
702:,
698:,
667:,
663:,
621:oʊ
482:11
182:UN
170:US
158:UK
146:DE
135:CA
122:BR
115:S9
109:AU
9452:)
9448:(
9278:p
9270:p
9253:m
9251:(
9240:)
9236:(
9197:m
9189:L
9181:L
9172:L
9163:L
9104:D
8620:)
8616:D
8325:L
8300:)
8225:)
8217:(
8156:)
8148:(
7904:p
7896:o
7888:N
7880:m
7396:e
7389:t
7382:v
6640:)
6636:(
6453:)
6449:D
6422:p
6384:p
6376:p
5688:p
5680:p
5672:p
5410:)
5401:(
5216:e
5209:t
5202:v
4357:)
4353:(
4043:)
4039:(
3900:L
3815:)
3807:(
3712:L
3627:)
3619:(
3538:)
3530:(
3501:D
3396:)
3388:(
2369:e
2362:t
2355:v
2314:.
2281:.
2250:.
2228::
2190:.
2157:.
2137::
2114:.
2074:.
2038:.
2020:.
1989:.
1958:.
1927:.
1873:.
1853::
1811:.
1780:.
1760::
1722:.
1708::
1676:.
1654::
1627:.
1519:β
1476:α
1434:5
1398:α
1347:2
1183:2
655:(
627:/
624:n
618:n
615:ɪ
612:θ
609:æ
606:k
603:ˈ
600:/
596:(
511:)
488:O
485:N
479:H
476:9
473:C
419:)
415:(
184::
172::
160::
124::
111::
25:.
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