1109:(VMAT-2) ligand (dihydrotetrabenazine) binding. Dopamine depletion resulting from administration of AMPT had similar neuropharmacological effects as cocaine. Administration of methamphetamine, a dopamine-releasing agent, rapidly decreased vesicular uptake. A relationship between cytoplasmic dopamine concentration and VMAT activity was established using cocaine, methamphetamines, and AMPT. Although it is not well understood, this relationship allows for AMPT’s inhibitory property, which blocks tyrosine hydroxylase, to increase dopamine transport by the vesicle monoamine transporter-2. This leads to a reduction in the newly synthesized pool of dopamine from replenished tyrosine. AMPT’s effect on dopamine concentration and transport is reversible and short-lived. If methamphetamine is administered while cytoplasmic dopamine is depleted to about 50% of the control levels, its neurotoxic effects are averted (Thomas et al., 2008). The recovery of dopamine to normal levels after AMPT administration takes about 2 to 7 days, and this repletion of dopamine is not changed by methamphetamine. For these reasons AMPT seems to be a better treatment drug in methamphetamine addicts than reserpine, which is also being researched as a possible methamphetamine treatment drug. Reserpine causes almost full loss of dopamine from the striatum by disrupting vesicle storage. The repletion of dopamine after reserpine administration is slower than AMPT. Additionally, administration of reserpine when dopamine is maximally depleted causes neurotoxic effects, which does not occur with AMPT treatment. AMPT’s role in addiction has also been studied via changes in dopamine binding to D2 and D3 receptors in the striatum (caudate, putamen, and ventral striatum) after the administration of AMPT. Findings revealed that cocaine-dependent subjects exhibited lower levels of endogenous dopamine relative to healthy subjects after AMPT administration. Similar positive effects were found in the role of AMPT in methamphetamine-addicted subjects. Dystonias and dyskinesias onset seems to derive from inconsistent regulation of dopamine in dopamine pathways. AMPT’s ability to deplete dopamine in the CNS makes it a promising target for treatment of dopamine related disorders.
1022:
day cause a 20 to 79 percent reduction in total catecholamines in
Pheochromocytoma patients. Increase in dosage increases the magnitude of catecholamine synthesis inhibition. This increasing inhibitory effect is seen in dosages up to 1500 mg per day; at higher doses, the inhibitory effect of AMPT decreases. The maximum effect of orally administered AMPT occurs 48 to 72 hours after administration of the drug. Catecholamine production levels return to normal 72 to 96 hours after administration of the drug ceases. Dosages as low as 300 mg per day have been found to have an effect on catecholamine production, which can be measured through urinary excretion analysis and cerebral spinal fluid assays. AMPT is successful at inhibiting catecholamine production in humans whether the rate of synthesis is high, as in pheochromocytoma, or normal as in patients with hypertension.
1122:
Patients have reported insomnia as a withdrawal symptom post AMPT exposure. When L-dopa is administered following AMPT administration, the effects of AMPT are reversed. These findings suggest that AMPT's effect on alertness and anxiety is catecholamine-specific and further supports that catecholamines are involved in the regulation of normal states of arousal and pathological anxiety symptoms. Patients have reported hand, leg, and trunk tremors as well as tightening of the jaw post AMPT drug therapy. These
Parkinson like side effects are supported by the lack of dopamine in the brain as in Parkinson’s patients. Tourette syndrome patients treated with AMPT developed akinesia, akathisia, and oculogyric crisis. Most severe of all, patients developed crystalluria (crystals in the urine) after undergoing AMPT drug treatments.
1008:
985:
380:
242:
1093:. Pheochromocytoma is a rare neuroendocrine tumor that results in the release of too much epinephrine and norepinephrine, hormones that control heart rate, metabolism, and blood pressure. AMPT was used in the 1960s for preoperative pharmacological control of catecholamine overexpression that causes hypertension and other arterial and cardiac abnormalities. The use of AMPT to treat Pheochromocytoma prior to surgery was discontinued due to its extensive side effects.
1138:
42:
669:
4162:
1282:
1097:
dopamine D2 receptors in the caudate and putamen as well as in limbic target areas, they can also block or partially block serotonin. Therapy with AMPT could prove to be more specific to dopamine and therefore eliminate some of the negative side effects of antipsychotic drugs. Metirosine is used as an off-label treatment for
1043:
AMPT is minimally metabolized by the body and absorbed well after oral ingestion making its bioavailability high. Single-dose studies have shown that a 1,000 mg dose results in AMPT levels in the plasma of 12-14 μg/mL after 1 to 3 hours of ingestion. Maintenance-dose studies have shown that
1121:
AMPT administration in healthy subjects has shown to cause increased sleepiness, decreased calmness, increased tension and anger, and a trend for increased depression. Sedation was also reported as a side effect of AMPT ingestion. However, sedation was not seen in AMPT doses of less than 2g per day.
1096:
Phosphorylation of tyrosine hydroxylase at Ser31 or Ser40 can increase dopamine biosynthesis; therefore an increase in pSer31 or pSer40 elevates dopamine synthesis in DA neurons. Excessive dopamine in the mesolimbic pathways of the brain produces psychotic symptoms. Antipsychotic medications block
1021:
AMPT inhibits catecholamine biosynthesis at the first step—the hydroxylation of tyrosine. Reduction in catecholamines and their metabolites (normetanephrine, metanephrine, and 4-hydroxy-3-methoxymandelic acid) result from the inhibition of tyrosine using AMPT. AMPT doses of 600 to 4,000 mg per
1112:
Metirosine is used in scientific research to investigate the effects of catecholamine depletion on behavior. There is evidence that catecholamine depletion causes an increase in sleepiness that is more pronounced than sleep deprivation, and that the fatigue lingers after the drug is discontinued.
1060:
Small amounts of metabolites (alpha-methyldopa and alpha-methyldopamine) were found after the administration of both single-doses and maintenance-doses of AMPT. Small amounts of methyltyramine and alpha-methylnoradrenaline were found in patients undergoing AMPT therapy. Urine analysis also
1104:
The dopamine transporter (DAT) is a principal site of action for cocaine. Cocaine inhibits DAT function and vesicular dopamine transport (VMAT). Cocaine administration abruptly and reversibly increases both the Vmax of dopamine uptake and the Bmax of
1928:
O'Leary OF, Bechtholt AJ, Crowley JJ, Hill TE, Page ME, Lucki I (June 2007). "Depletion of serotonin and catecholamines block the acute behavioral response to different classes of antidepressant drugs in the mouse tail suspension test".
1061:
recovered 45 to 88 percent of unchanged AMPT after drug ingestion. Of the total AMPT excreted, 50 to 60 percent appeared in urine within the first 8 hours and 80 to 90 percent appeared within 24 hours of oral administration.
2101:
Zimmermann RC, Krahn LE, Klee GG, Ditkoff EC, Ory SJ, Sauer MV (2001). "Prolonged inhibition of presynaptic catecholamine synthesis with alpha-methyl-para-tyrosine attenuates the circadian rhythm of human TSH secretion".
1141:
Biosynthesis of dopamine: Dopamine, norepinephrine, and epinephrine are all synthesized through a multistep processing of tyrosine. Tyrosine is a highly concentrated amino acid in catecholaminergic neurons
2066:
Sweet RD, Bruun R, Shapiro E, Shapiro AK (December 1974). "Presynaptic catecholamine antagonists as treatment for
Tourette syndrome. Effects of alpha methyl para tyrosine and tetrabenazine".
2740:
2169:
2024:"The effects of L-dihydroxyphenylalanine on alertness and mood in alpha-methyl-para-tyrosine-treated healthy humans. Further evidence for the role of catecholamines in arousal and anxiety"
774:
573:, which is hydroxylated by tyrosine hydroxylase and it is hypothesized that AMPT competes with tyrosine at the tyrosine-binding site, causing inhibition of tyrosine hydroxylase.
1765:
2733:
2162:
708:
1881:"Lower level of endogenous dopamine in patients with cocaine dependence: findings from PET imaging of D(2)/D(3) receptors following acute dopamine depletion"
1205:
439:
1030:
Pheochromocytoma patients exhibited a drop in blood pressure when taking AMPT. AMPT had no effect in patients with hypertension (high blood pressure).
4182:
2726:
2155:
4131:
3569:
2684:
1357:
4135:
3880:
2770:
140:
1448:
Brogden RN, Heel RC, Speight TM, Avery GS (February 1981). "alpha-Methyl-p-tyrosine: a review of its pharmacology and clinical use".
1296:
1215:
1106:
394:
4187:
1069:
Metirosine has been shown to suppress catecholamine synthesis and alleviate symptoms related to catecholamine excess, including
2957:
2935:
858:
804:
726:
4139:
3850:
3671:
2970:
2605:
2466:
261:
1238:
Ankenman R, Salvatore MF (2007). "Low dose alpha-methyl-para-tyrosine (AMPT) in the treatment of dystonia and dyskinesia".
3991:
3619:
2582:
1280:-tyrosine to inhibit melanin production in iris melanocytes", issued 19 March 2002, assigned to Pfizer Health AB.
4152:
514:
4111:
2268:
335:
3961:
3499:
2701:
2410:
964:
745:
357:
1113:
Catecholamine depletion has also been linked to a negative mood, though this is reported less often than sleepiness.
3680:
3675:
3360:
2988:
2948:
2926:
2749:
695:
1044:
absorption of AMPT is overall the same in all individuals taking doses in the range of 300-4,000 mg per day.
3386:
2864:
1052:
The half-life of AMPT in normal patients is 3.4 to 3.7 hours. In amphetamine addicts the half-life is 7.2 hours.
4197:
2221:
1794:"Regulation of the vesicular monoamine transporter-2: a novel mechanism for cocaine and other psychostimulants"
2147:
3923:
2689:
1766:"Doctors said the boy was suffering from teenage psychosis. What he really had was a rare genetic condition"
4081:
2657:
1003:
580:. It has been demonstrated to inhibit the production of melanin. It is available as a generic medication.
237:
4127:
4123:
4119:
3966:
3800:
3779:
2903:
2609:
1090:
616:
161:
1977:"Effects of catecholamine depletion on alertness and mood in rested and sleep deprived normal volunteers"
1832:"The newly synthesized pool of dopamine determines the severity of methamphetamine-induced neurotoxicity"
3684:
2961:
2939:
2382:
2142:
1146:
542:
413:
2R: InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m1/s1
403:
2S: InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1
4011:
4115:
3426:
3416:
2639:
2359:
2326:
1150:
837:
554:
1605:"Efficacy and safety of metyrosine in pheochromocytoma/paraganglioma: a multi-center trial in Japan"
980:
375:
3554:
3278:
2573:
2200:
879:
88:
3745:
3342:
3337:
3730:
3711:
3707:
3693:
3689:
3459:
3260:
2912:
2355:
1954:
1585:
1473:
756:
3599:
2301:
561:. AMPT inhibits tyrosine hydroxylase whose enzymatic activity is normally regulated through the
4036:
3604:
3896:
3870:
3840:
3648:
3639:
3609:
3200:
2979:
2975:
2884:
2139:
2119:
2083:
2045:
1998:
1946:
1910:
1861:
1805:
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1702:
1675:
1626:
1577:
1531:
1465:
1353:
1255:
1211:
1137:
1098:
819:
681:
423:
2RS: InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)
4192:
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1007:
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241:
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2079:
888:
115:
107:
99:
1879:
Martinez D, Greene K, Broft A, Kumar D, Liu F, Narendran R, et al. (October 2009).
1603:
Naruse M, Satoh F, Tanabe A, Okamoto T, Ichihara A, Tsuiki M, et al. (March 2018).
3653:
3585:
3519:
3469:
3375:
3206:
2944:
2823:
2695:
2446:
2428:
1905:
1880:
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1178:
508:
2115:
1670:
1645:
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1501:
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3402:
3066:
3046:
3011:
2819:
2542:
2456:
2367:
2195:
2178:
2040:
2023:
2019:
1972:
1847:
1461:
1166:
996:
558:
230:
1958:
1589:
1477:
569:
residues in regulatory domain sites. Catecholamine biosynthesis starts with dietary
3981:
3760:
3666:
3544:
3479:
3231:
3211:
3106:
3101:
3091:
3016:
2931:
2627:
2550:
2436:
2372:
2306:
2286:
2186:
1896:
1560:
Engelman K, Sjoerdsma A (1966). "Inhibition of
Catecholamine Biosynthesis in Man".
1321:
1070:
913:
787:
782:
644:
609:
308:
2718:
1793:
1373:
316:
1398:
1349:
Nomenclature of
Organic Chemistry. IUPAC Recommendations and Preferred Names 2013
1347:
324:
4021:
3939:
3662:
3589:
3474:
3370:
3221:
3150:
3145:
3140:
3036:
3026:
2922:
2854:
2807:
2665:
2653:
2441:
2377:
2340:
2296:
2276:
2258:
2248:
1975:, Penetar DM, Shaham Y, Thorne DR, Sing HC, Thomas ML, et al. (June 1993).
1694:
1174:
1078:
647:, the racemate was also of interest as a potentially cheaper material, known as
1573:
4091:
4041:
3976:
3971:
3835:
3816:
3750:
3740:
3549:
3534:
3529:
3484:
3328:
3323:
3318:
3303:
3298:
3293:
3288:
3270:
3265:
3241:
3236:
3226:
3170:
3160:
3155:
3135:
3086:
3081:
3061:
3041:
3031:
3021:
3006:
2874:
2844:
2840:
2828:
2752:
2661:
2635:
2595:
2590:
2527:
2512:
2474:
2345:
2335:
2253:
2243:
1942:
1621:
1604:
944:
593:
493:
250:
172:
1581:
1251:
718:
4077:
4046:
4031:
4007:
3946:
3914:
3900:
3866:
3789:
3785:
3765:
3755:
3559:
3313:
3216:
3196:
3188:
3111:
3076:
3071:
3056:
3051:
2984:
2869:
2859:
2814:
2802:
2643:
2517:
2507:
2451:
2418:
2311:
2291:
2281:
2238:
2233:
712:
41:
2123:
1950:
1914:
1865:
1809:
1750:
1706:
1630:
1273:
1259:
660:
2087:
2049:
2002:
1741:
1724:
1679:
1535:
1469:
17:
3830:
3635:
3539:
3515:
3489:
3442:
3406:
3366:
3308:
3175:
3001:
2966:
2835:
2793:
2631:
2532:
2522:
2316:
1661:
1170:
1162:
1154:
1085:. Metirosine is primarily used to reduce these symptoms in patients with
1074:
924:
740:
605:
597:
589:
570:
209:
2022:, Thorne D, Hall M, Popp K, Avery W, Sing H, et al. (August 1995).
1993:
1976:
933:
219:
4051:
3283:
3192:
3184:
899:
668:
624:
294:
1517:
1502:"Biochemical and pharmacologic effects of alpha-methyltyrosine in man"
3446:
2786:
1158:
1082:
601:
566:
151:
557:
enzyme inhibitor and is therefore a drug involved in inhibiting the
507:
Except where otherwise noted, data are given for materials in their
1644:
Green KN, Larsson SK, Beevers DG, Bevan PG, Hayes B (August 1982).
1207:
282:
3820:
3644:
3165:
2798:
1136:
139:
128:
1352:. IUPAC-IUB Joint Commission on Biochemical Nomenclature. 2013.
272:
2722:
2151:
813:
735:
3570:
1646:"Alpha-methyltyrosine in the management of phaeochromocytoma"
1500:
Engelman K, Horwitz D, Jéquier E, Sjoerdsma A (March 1968).
969:
362:
3881:
2771:
1798:
The
Journal of Pharmacology and Experimental Therapeutics
1240:
The
Journal of Neuropsychiatry and Clinical Neurosciences
1830:
Thomas DM, Francescutti-Verbeem DM, Kuhn DM (May 2008).
1374:"(R)-2-Amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid"
3851:
1725:"Phaeochromocytoma--recent progress in its management"
870:)-2-amino- 3-(4-hydroxyphenyl)- 2-methylpropanoic acid
4150:
3992:
3620:
1125:
Prolonged administration can have an impact upon the
2104:
Journal of the
Society for Gynecologic Investigation
1718:
1716:
604:
group in the α-position where tyrosine would have a
4060:
3990:
3922:
3913:
3879:
3849:
3799:
3778:
3618:
3568:
3500:
3498:
3425:
3385:
3359:
2883:
2769:
2762:
2604:
2581:
2571:
2541:
2494:
2487:
2465:
2427:
2409:
2402:
2395:
2354:
2325:
2267:
2220:
2213:
2194:
1792:Brown JM, Hanson GR, Fleckenstein AE (March 2001).
995:
963:
943:
923:
898:
878:
849:
836:
828:
803:
798:
773:
755:
725:
707:
690:
680:
675:
260:
3387:
1495:
1493:
1491:
1489:
1487:
912:
323:
315:
307:
3924:
1701:. Treasure Island (FL): StatPearls Publishing.
1233:
1231:
1229:
1227:
887:
114:
106:
98:
3801:
3575:Tooltip Phenylethanolamine N-methyltransferase
2904:
2610:
2734:
2163:
1210:(Second ed.). McGraw Hill Professional.
1089:. It is contraindicated for the treatment of
627:material which contains equal amounts of the
8:
3427:
2543:Non-selective α-adrenergic receptor blockers
744:
659:
3886:Tooltip Acetylserotonin O-methyltransferase
2776:Tooltip Aromatic L-amino acid decarboxylase
1555:
1553:
1551:
1549:
1547:
1545:
3919:
3796:
3382:
2913:
2894:
2766:
2741:
2727:
2719:
2578:
2491:
2406:
2399:
2217:
2210:
2170:
2156:
2148:
1443:
1441:
1439:
1006:
983:
952:
667:
378:
240:
197:
189:
181:
29:
2885:
2039:
2014:
2012:
1992:
1904:
1855:
1825:
1823:
1821:
1819:
1740:
1669:
1620:
1525:
1437:
1435:
1433:
1431:
1429:
1427:
1425:
1423:
1421:
1419:
1204:Nestler EJ, Hyman SE, Malenka RC (2008).
1199:
1197:
1195:
1193:
344:
2061:
2059:
1787:
1785:
1783:
1781:
1779:
719:Micromedex Detailed Consumer Information
4157:
4062:
1189:
979:
932:
863:
444:
399:
374:
218:
3856:Tooltip Serotonin N-acetyl transferase
997:
658:
639:isomer has been developed as the drug
623:form of AMPT is also known, as is the
231:
3997:Tooltip Histamine N-methyltransferase
3625:Tooltip Catechol-O-methyl transferase
1506:The Journal of Clinical Investigation
1165:. This results in lowered systematic
717:
699:
612:and in natural amino-acids takes the
576:It has been used in the treatment of
426:Key: NHTGHBARYWONDQ-UHFFFAOYSA-N
416:Key: NHTGHBARYWONDQ-SNVBAGLBSA-N
406:Key: NHTGHBARYWONDQ-JTQLQIEISA-N
160:
7:
2080:10.1001/archpsyc.1974.01760180095012
1276:, Drago F, "Use of α-methyl-
1017:Effect on catecholamine biosynthesis
786:
3505:Tooltip Dopamine beta-monooxygenase
1405:. U.S. National Library of Medicine
1380:. U.S. National Library of Medicine
1328:. U.S. National Library of Medicine
903:
297:
281:
1885:The American Journal of Psychiatry
1693:Gupta PK, Marwaha B (March 2023).
559:catecholamine biosynthetic pathway
25:
3392:Tooltip Phenylalanine hydroxylase
1301:U.S. Food and Drug Administration
1153:, it prevents the conversion of
1107:vesicular monoamine transporter 2
447:2S: C(Cc1ccc(cc1)O)(C(=O)O)N
4160:
1848:10.1111/j.1471-4159.2007.05155.x
1462:10.2165/00003495-198121020-00001
1297:"Metyrosine: FDA-Approved Drugs"
480:
474:
40:
4183:Tyrosine hydroxylase inhibitors
3929:Tooltip Histidine decarboxylase
2606:Endothelin receptor antagonists
2467:Tyrosine hydroxylase inhibitors
511:(at 25 °C , 100 kPa).
3806:Tooltip Tryptophan hydroxylase
3586:Norepinephrine (noradrenaline)
3520:Norepinephrine (Noradrenaline)
2945:Norepinephrine (noradrenaline)
2909:Tooltip Aldehyde dehydrogenase
2615:Tooltip Pulmonary hypertension
2583:Serotonin receptor antagonists
2068:Archives of General Psychiatry
1897:10.1176/appi.ajp.2009.08121801
1729:British Journal of Anaesthesia
483:
468:
1:
4132:Monoamine reuptake inhibitors
4112:Receptor/signaling modulators
2500:-Adrenergic receptor blockers
2269:Adrenergic release inhibitors
2226:-Adrenergic receptor agonists
2116:10.1016/S1071-5576(01)00104-6
584:Structure and stereochemistry
69:: (Inactive isomer)
3432:Tooltip Tyrosine hydroxylase
2411:Monoamine oxidase inhibitors
2041:10.1016/0893-133X(94)00134-L
1723:Prys-Roberts C (July 2000).
1346:"Amino Acids and Peptides".
4092:Pimagedine (aminoguanidine)
3962:Alpha-Fluoromethylhistidine
619:. However, the alternative
4214:
4136:Monoamine releasing agents
2902:Substrates→Products (with
1574:10.1161/01.RES.18.S6.I-104
4104:
3250:
3125:
2897:
2890:Tooltip Monoamine oxidase
2679:
1943:10.1007/s00213-007-0728-9
1836:Journal of Neurochemistry
1764:Talan J (30 April 2021).
1622:10.1507/endocrj.EJ17-0276
854:
666:
608:atom. This position is a
505:
455:
435:
390:
53:
48:
39:
3590:Epinephrine (adrenaline)
2923:Epinephrine (adrenaline)
1252:10.1176/jnp.2007.19.1.65
1026:Effect on blood pressure
4188:Antihypertensive agents
4067:Tooltip Diamine oxidase
2028:Neuropsychopharmacology
1981:Neuropsychopharmacology
600:. It contains an extra
3967:Histidine methyl ester
2181:(and closely related)
1142:
1091:essential hypertension
617:absolute configuration
63:: Metirosine
4140:Monoamine neurotoxins
4082:Imidazole acetic acid
2360:nicotinic antagonists
1147:competitive inhibitor
1140:
75:: α-Methyl-
4075:Substrates→Products:
4005:Substrates→Products:
3937:Substrates→Products:
3894:Substrates→Products:
3864:Substrates→Products:
3814:Substrates→Products:
3633:Substrates→Products:
3583:Substrates→Products:
3513:Substrates→Products:
3440:Substrates→Products:
3417:3,4-Dihydroxystyrene
3400:Substrates→Products:
2784:Substrates→Products:
2327:Imidazoline receptor
1662:10.1136/thx.37.8.632
1562:Circulation Research
1151:tyrosine hydroxylase
1081:, constipation, and
555:tyrosine hydroxylase
541:, also known in its
3555:Phenopicolinic acid
3279:Desmethylselegiline
1994:10.1038/npp.1993.34
1770:The Washington Post
1742:10.1093/bja/85.1.44
1568:(S6): I–104–I–109.
1161:, the precursor to
663:
588:AMPT is related to
501: g·mol
36:
3731:2-Hydroxyestradiol
3712:4-Methoxyestradiol
3708:4-Hydroxyestradiol
3694:2-Methoxyestradiol
3690:2-Hydroxyestradiol
3460:2-Hydroxyestradiol
2706:Never to phase III
1931:Psychopharmacology
1695:"Pheochromocytoma"
1143:
643:and, as with many
515:Infobox references
74:
68:
62:
30:
4148:
4147:
4143:
4100:
4099:
4012:N-Methylhistamine
3942:
3909:
3908:
3897:N-Acetylserotonin
3871:N-Acetylserotonin
3841:Telotristat ethyl
3836:Fenclonine (PCPA)
3793:
3774:
3773:
3649:Homovanillic acid
3640:3-Methoxytyramine
3449:
3379:
3355:
3354:
3351:
3350:
3332:
3273:
3201:tetrahydroharmine
3181:Harmala alkaloids
2976:3-Methoxytyramine
2831:
2810:
2789:
2716:
2715:
2675:
2674:
2567:
2566:
2563:
2562:
2559:
2558:
2483:
2482:
2391:
2390:
2356:Ganglion-blocking
2183:antihypertensives
1891:(10): 1170–1177.
1609:Endocrine Journal
1518:10.1172/JCI105754
1359:978-0-85404-182-4
1099:DiGeorge syndrome
1014:
1013:
965:CompTox Dashboard
817:
738:
702:
523:Chemical compound
521:
520:
358:CompTox Dashboard
141:Interactive image
72:
66:
60:
27:Chemical compound
16:(Redirected from
4205:
4165:
4164:
4163:
4156:
4106:
4068:
4064:
3998:
3994:
3940:
3930:
3926:
3920:
3887:
3883:
3857:
3853:
3807:
3803:
3797:
3783:
3736:2-Hydroxyestrone
3721:4-Methoxyestrone
3717:4-Hydroxyestrone
3703:2-Methoxyestrone
3699:2-Hydroxyestrone
3626:
3622:
3576:
3572:
3506:
3502:
3465:2-Hydroxyestrone
3450:-DOPA (levodopa)
3447:
3433:
3429:
3393:
3389:
3383:
3364:
3330:
3271:
3258:MAO-B selective:
3133:MAO-A-selective:
3097:Phenoxypropazine
2919:
2915:
2910:
2906:
2895:
2891:
2887:
2829:
2808:
2790:-DOPA (levodopa)
2787:
2777:
2773:
2767:
2743:
2736:
2729:
2720:
2616:
2612:
2579:
2492:
2407:
2400:
2218:
2211:
2205:vasoconstriction
2172:
2165:
2158:
2149:
2144:A Clinical Trial
2128:
2127:
2098:
2092:
2091:
2063:
2054:
2053:
2043:
2016:
2007:
2006:
1996:
1969:
1963:
1962:
1925:
1919:
1918:
1908:
1876:
1870:
1869:
1859:
1827:
1814:
1813:
1789:
1774:
1773:
1761:
1755:
1754:
1744:
1720:
1711:
1710:
1690:
1684:
1683:
1673:
1641:
1635:
1634:
1624:
1600:
1594:
1593:
1557:
1540:
1539:
1529:
1497:
1482:
1481:
1445:
1414:
1413:
1411:
1410:
1399:"Racemetirosine"
1395:
1389:
1388:
1386:
1385:
1370:
1364:
1363:
1343:
1337:
1336:
1334:
1333:
1318:
1312:
1311:
1309:
1307:
1293:
1287:
1286:
1285:
1281:
1270:
1264:
1263:
1235:
1222:
1221:
1201:
1127:circadian rhythm
1087:pheochromocytoma
1034:Pharmacokinetics
1010:
999:
988:
987:
973:
971:
956:
936:
916:
906:
905:
891:
841:
815:
812:
790:
748:
737:
734:
721:
701:
698:
671:
664:
662:
578:pheochromocytoma
539:α-methyltyrosine
500:
485:
482:
476:
470:
463:Chemical formula
383:
382:
366:
364:
348:
327:
319:
311:
299:
285:
264:
244:
233:
222:
201:
193:
185:
164:
143:
118:
110:
102:
44:
37:
21:
4213:
4212:
4208:
4207:
4206:
4204:
4203:
4202:
4198:Phenethylamines
4173:
4172:
4171:
4161:
4159:
4151:
4149:
4144:
4096:
4066:
4056:
4027:Diphenhydramine
3996:
3986:
3928:
3905:
3885:
3875:
3855:
3845:
3805:
3782:
3770:
3658:Normetanephrine
3624:
3614:
3574:
3564:
3504:
3494:
3431:
3421:
3391:
3374:
3363:
3361:Phenethylamines
3347:
3246:
3121:
3117:Tranylcypromine
2954:Normetanephrine
2917:
2908:
2889:
2879:
2775:
2758:
2747:
2717:
2712:
2711:
2696:Clinical trials
2671:
2614:
2600:
2555:
2537:
2499:
2479:
2461:
2429:VMAT inhibitors
2423:
2387:
2350:
2321:
2263:
2225:
2203:
2198:
2190:
2176:
2136:
2131:
2100:
2099:
2095:
2065:
2064:
2057:
2018:
2017:
2010:
1971:
1970:
1966:
1927:
1926:
1922:
1878:
1877:
1873:
1829:
1828:
1817:
1791:
1790:
1777:
1763:
1762:
1758:
1722:
1721:
1714:
1692:
1691:
1687:
1643:
1642:
1638:
1602:
1601:
1597:
1559:
1558:
1543:
1499:
1498:
1485:
1447:
1446:
1417:
1408:
1406:
1397:
1396:
1392:
1383:
1381:
1372:
1371:
1367:
1360:
1345:
1344:
1340:
1331:
1329:
1320:
1319:
1315:
1305:
1303:
1295:
1294:
1290:
1283:
1272:
1271:
1267:
1237:
1236:
1225:
1218:
1203:
1202:
1191:
1187:
1135:
1119:
1067:
1058:
1050:
1041:
1036:
1028:
1019:
991:
967:
959:
939:
919:
902:
894:
874:
871:
862:
861:
839:
830:Pharmacokinetic
824:
794:
769:
758:
751:
657:
586:
563:phosphorylation
524:
517:
512:
498:
488:
479:
473:
465:
451:
448:
443:
442:
431:
428:
427:
424:
418:
417:
414:
408:
407:
404:
398:
397:
386:
367:
360:
351:
330:
300:
288:
267:
253:
225:
204:
167:
146:
132:
121:
91:
82:
28:
23:
22:
15:
12:
11:
5:
4211:
4209:
4201:
4200:
4195:
4190:
4185:
4175:
4174:
4170:
4169:
4146:
4145:
4105:
4102:
4101:
4098:
4097:
4095:
4094:
4085:
4084:
4071:
4069:
4058:
4057:
4055:
4054:
4049:
4044:
4039:
4034:
4029:
4024:
4015:
4014:
4001:
3999:
3988:
3987:
3985:
3984:
3979:
3974:
3969:
3964:
3959:
3950:
3949:
3933:
3931:
3917:
3911:
3910:
3907:
3906:
3904:
3903:
3890:
3888:
3877:
3876:
3874:
3873:
3860:
3858:
3847:
3846:
3844:
3843:
3838:
3833:
3824:
3823:
3810:
3808:
3794:
3776:
3775:
3772:
3771:
3769:
3768:
3763:
3758:
3753:
3748:
3743:
3738:
3733:
3724:
3723:
3714:
3705:
3696:
3687:
3678:
3669:
3660:
3654:Norepinephrine
3651:
3642:
3629:
3627:
3616:
3615:
3613:
3612:
3607:
3602:
3593:
3592:
3579:
3577:
3566:
3565:
3563:
3562:
3557:
3552:
3547:
3542:
3537:
3532:
3523:
3522:
3509:
3507:
3496:
3495:
3493:
3492:
3487:
3482:
3477:
3472:
3470:3-Iodotyrosine
3467:
3462:
3453:
3452:
3436:
3434:
3423:
3422:
3420:
3419:
3410:
3409:
3396:
3394:
3380:
3376:norepinephrine
3357:
3356:
3353:
3352:
3349:
3348:
3346:
3345:
3340:
3335:
3326:
3321:
3316:
3311:
3306:
3301:
3296:
3291:
3286:
3281:
3276:
3268:
3263:
3251:
3248:
3247:
3245:
3244:
3239:
3234:
3229:
3224:
3219:
3214:
3209:
3207:Methylene blue
3204:
3178:
3173:
3168:
3166:CX157 (Tyrima)
3163:
3158:
3153:
3148:
3143:
3138:
3126:
3123:
3122:
3120:
3119:
3114:
3109:
3104:
3099:
3094:
3089:
3084:
3079:
3074:
3069:
3064:
3059:
3054:
3049:
3044:
3039:
3034:
3029:
3024:
3019:
3014:
3009:
3004:
2999:Non-selective:
2992:
2991:
2982:
2973:
2964:
2951:
2942:
2929:
2898:
2892:
2881:
2880:
2878:
2877:
2872:
2867:
2862:
2857:
2848:
2847:
2838:
2826:
2824:Phenethylamine
2817:
2805:
2796:
2780:
2778:
2764:
2760:
2759:
2748:
2746:
2745:
2738:
2731:
2723:
2714:
2713:
2710:
2709:
2708:
2707:
2704:
2693:
2687:
2681:
2680:
2677:
2676:
2673:
2672:
2670:
2669:
2647:
2620:
2618:
2602:
2601:
2599:
2598:
2593:
2587:
2585:
2576:
2569:
2568:
2565:
2564:
2561:
2560:
2557:
2556:
2554:
2553:
2547:
2545:
2539:
2538:
2536:
2535:
2530:
2525:
2520:
2515:
2510:
2504:
2502:
2497:
2489:
2485:
2484:
2481:
2480:
2478:
2477:
2471:
2469:
2463:
2462:
2460:
2459:
2454:
2449:
2447:Methoserpidine
2444:
2439:
2433:
2431:
2425:
2424:
2422:
2421:
2415:
2413:
2404:
2397:
2393:
2392:
2389:
2388:
2386:
2385:
2380:
2375:
2370:
2364:
2362:
2352:
2351:
2349:
2348:
2343:
2338:
2332:
2330:
2323:
2322:
2320:
2319:
2314:
2309:
2304:
2299:
2294:
2289:
2284:
2279:
2273:
2271:
2265:
2264:
2262:
2261:
2256:
2251:
2246:
2241:
2236:
2230:
2228:
2223:
2215:
2208:
2196:Sympatholytics
2192:
2191:
2177:
2175:
2174:
2167:
2160:
2152:
2146:
2145:
2135:
2134:External links
2132:
2130:
2129:
2110:(3): 174–178.
2093:
2074:(6): 857–861.
2055:
2008:
1987:(4): 345–356.
1964:
1937:(3): 357–371.
1920:
1871:
1842:(3): 605–616.
1815:
1804:(3): 762–767.
1775:
1756:
1712:
1685:
1656:(8): 632–633.
1636:
1615:(3): 359–371.
1595:
1541:
1512:(3): 577–594.
1483:
1415:
1390:
1365:
1358:
1338:
1313:
1288:
1265:
1223:
1216:
1188:
1186:
1183:
1179:norepinephrine
1134:
1131:
1118:
1115:
1066:
1063:
1057:
1054:
1049:
1046:
1040:
1037:
1035:
1032:
1027:
1024:
1018:
1015:
1012:
1011:
1001:
993:
992:
990:
989:
981:DTXSID90859529
976:
974:
961:
960:
958:
957:
949:
947:
941:
940:
938:
937:
929:
927:
921:
920:
918:
917:
909:
907:
896:
895:
893:
892:
884:
882:
876:
875:
873:
872:
865:
857:
856:
855:
852:
851:
847:
846:
843:
834:
833:
826:
825:
823:
822:
809:
807:
801:
800:
796:
795:
793:
792:
779:
777:
771:
770:
768:
767:
763:
761:
753:
752:
750:
749:
731:
729:
723:
722:
715:
705:
704:
692:
688:
687:
684:
678:
677:
673:
672:
656:
653:
649:racemetirosine
585:
582:
522:
519:
518:
513:
509:standard state
506:
503:
502:
496:
490:
489:
486:
477:
471:
466:
461:
458:
457:
453:
452:
450:
449:
446:
438:
437:
436:
433:
432:
430:
429:
425:
422:
421:
419:
415:
412:
411:
409:
405:
402:
401:
393:
392:
391:
388:
387:
385:
384:
376:DTXSID90859529
370:
368:
356:
353:
352:
350:
349:
340:
338:
332:
331:
329:
328:
320:
312:
303:
301:
293:
290:
289:
287:
286:
277:
275:
269:
268:
266:
265:
256:
254:
249:
246:
245:
235:
227:
226:
224:
223:
214:
212:
206:
205:
203:
202:
194:
186:
177:
175:
169:
168:
166:
165:
156:
154:
148:
147:
145:
144:
135:
133:
126:
123:
122:
120:
119:
111:
103:
94:
92:
87:
84:
83:
81:
80:
70:
64:
58:
54:
51:
50:
46:
45:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
4210:
4199:
4196:
4194:
4191:
4189:
4186:
4184:
4181:
4180:
4178:
4168:
4158:
4154:
4142:
4141:
4137:
4133:
4129:
4128:Serotonergics
4125:
4124:Melatonergics
4121:
4120:Dopaminergics
4117:
4113:
4110:
4103:
4093:
4090:
4087:
4086:
4083:
4079:
4076:
4073:
4072:
4070:
4065:
4059:
4053:
4050:
4048:
4045:
4043:
4040:
4038:
4035:
4033:
4030:
4028:
4025:
4023:
4020:
4017:
4016:
4013:
4009:
4006:
4003:
4002:
4000:
3995:
3989:
3983:
3980:
3978:
3975:
3973:
3970:
3968:
3965:
3963:
3960:
3958:
3955:
3952:
3951:
3948:
3944:
3938:
3935:
3934:
3932:
3927:
3921:
3918:
3916:
3912:
3902:
3898:
3895:
3892:
3891:
3889:
3884:
3878:
3872:
3868:
3865:
3862:
3861:
3859:
3854:
3848:
3842:
3839:
3837:
3834:
3832:
3829:
3826:
3825:
3822:
3818:
3815:
3812:
3811:
3809:
3804:
3798:
3795:
3791:
3787:
3781:
3777:
3767:
3764:
3762:
3759:
3757:
3754:
3752:
3749:
3747:
3744:
3742:
3739:
3737:
3734:
3732:
3729:
3726:
3725:
3722:
3718:
3715:
3713:
3709:
3706:
3704:
3700:
3697:
3695:
3691:
3688:
3686:
3682:
3679:
3677:
3673:
3670:
3668:
3664:
3661:
3659:
3655:
3652:
3650:
3646:
3643:
3641:
3637:
3634:
3631:
3630:
3628:
3623:
3617:
3611:
3608:
3606:
3603:
3601:
3598:
3595:
3594:
3591:
3587:
3584:
3581:
3580:
3578:
3573:
3567:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3528:
3525:
3524:
3521:
3517:
3514:
3511:
3510:
3508:
3503:
3497:
3491:
3488:
3486:
3483:
3481:
3478:
3476:
3473:
3471:
3468:
3466:
3463:
3461:
3458:
3455:
3454:
3451:
3444:
3441:
3438:
3437:
3435:
3430:
3424:
3418:
3415:
3412:
3411:
3408:
3404:
3403:Phenylalanine
3401:
3398:
3397:
3395:
3390:
3384:
3381:
3377:
3372:
3368:
3362:
3358:
3344:
3341:
3339:
3336:
3334:
3327:
3325:
3322:
3320:
3317:
3315:
3312:
3310:
3307:
3305:
3302:
3300:
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3277:
3275:
3269:
3267:
3264:
3262:
3259:
3256:
3253:
3252:
3249:
3243:
3240:
3238:
3235:
3233:
3230:
3228:
3225:
3223:
3220:
3218:
3215:
3213:
3210:
3208:
3205:
3202:
3198:
3194:
3190:
3186:
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3093:
3090:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3067:Metfendrazine
3065:
3063:
3060:
3058:
3055:
3053:
3050:
3048:
3047:Isocarboxazid
3045:
3043:
3040:
3038:
3035:
3033:
3030:
3028:
3025:
3023:
3020:
3018:
3015:
3013:
3012:Echinopsidine
3010:
3008:
3005:
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3000:
2997:
2994:
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2990:
2986:
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2853:
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2825:
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2820:Phenylalanine
2818:
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2812:
2806:
2804:
2800:
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2501:
2493:
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2472:
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2464:
2458:
2457:Syrosingopine
2455:
2453:
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2445:
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2434:
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2368:Hexamethonium
2366:
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2184:
2180:
2179:Sympatholytic
2173:
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2015:
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1217:9780071641197
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1200:
1198:
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1190:
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1172:
1168:
1167:catecholamine
1164:
1160:
1156:
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1139:
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1128:
1123:
1116:
1114:
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1047:
1045:
1038:
1033:
1031:
1025:
1023:
1016:
1009:
1005:
1002:
1000:
998:ECHA InfoCard
994:
986:
982:
978:
977:
975:
966:
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955:
951:
950:
948:
946:
942:
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897:
890:
886:
885:
883:
881:
877:
869:
864:
860:
853:
848:
845:3.4–3.7 hours
844:
842:
835:
831:
827:
821:
811:
810:
808:
806:
802:
797:
789:
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732:
730:
728:
724:
720:
716:
714:
710:
706:
697:
693:
689:
685:
683:
679:
676:Clinical data
674:
670:
665:
654:
652:
650:
646:
642:
638:
635:isomers. The
634:
630:
626:
622:
618:
615:
611:
607:
603:
599:
596:component of
595:
591:
583:
581:
579:
574:
572:
568:
565:of different
564:
560:
556:
552:
548:
544:
540:
537:), or simply
536:
532:
530:
516:
510:
504:
497:
495:
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491:
467:
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459:
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371:
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341:
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321:
318:
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305:
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296:
292:
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284:
279:
278:
276:
274:
271:
270:
263:
258:
257:
255:
252:
248:
247:
243:
239:
236:
234:
232:ECHA InfoCard
229:
228:
221:
216:
215:
213:
211:
208:
207:
200:
195:
192:
187:
184:
179:
178:
176:
174:
171:
170:
163:
162:ChEMBL1200862
158:
157:
155:
153:
150:
149:
142:
137:
136:
134:
130:
125:
124:
117:
112:
109:
104:
101:
96:
95:
93:
90:
86:
85:
78:
71:
65:
59:
56:
55:
52:
47:
43:
38:
34:
19:
4108:
4107:
4088:
4074:
4018:
4004:
3982:Tritoqualine
3953:
3936:
3893:
3863:
3827:
3813:
3761:Quinalizarin
3746:Neluxicapone
3727:
3667:Metanephrine
3632:
3596:
3582:
3545:Fusaric acid
3526:
3512:
3480:Bulbocapnine
3456:
3439:
3413:
3399:
3343:Tisolagiline
3338:Sembragiline
3329:Selegiline (
3257:
3254:
3232:Sercloremine
3212:Metralindole
3132:
3129:
3107:Procarbazine
3102:Pivhydrazine
3092:Pheniprazine
3017:Furazolidone
2998:
2995:
2932:Metanephrine
2901:
2851:
2783:
2763:Non-specific
2649:
2628:Aprocitentan
2623:
2551:Phentolamine
2437:Bietaserpine
2383:Trimethaphan
2373:Mecamylamine
2307:Guanethidine
2287:Debrisoquine
2201:α-adrenergic
2199:(antagonize
2107:
2103:
2096:
2071:
2067:
2034:(1): 41–52.
2031:
2027:
1984:
1980:
1967:
1934:
1930:
1923:
1888:
1884:
1874:
1839:
1835:
1801:
1797:
1769:
1759:
1735:(1): 44–57.
1732:
1728:
1698:
1688:
1653:
1649:
1639:
1612:
1608:
1598:
1565:
1561:
1509:
1505:
1456:(2): 81–89.
1453:
1449:
1407:. Retrieved
1402:
1393:
1382:. Retrieved
1377:
1368:
1348:
1341:
1330:. Retrieved
1325:
1322:"Metyrosine"
1316:
1304:. Retrieved
1300:
1291:
1277:
1268:
1246:(1): 65–69.
1243:
1239:
1206:
1144:
1124:
1120:
1117:Side-effects
1111:
1103:
1095:
1071:hypertension
1068:
1065:Clinical use
1059:
1051:
1042:
1029:
1020:
867:
838:Elimination
805:Legal status
799:Legal status
727:License data
694:Metyrosine (
655:Pharmacology
648:
645:chiral drugs
640:
636:
632:
628:
620:
613:
610:stereocentre
587:
575:
550:
546:
538:
534:
528:
526:
525:
76:
49:Identifiers
32:
4116:Adrenergics
4089:Inhibitors:
4022:Amodiaquine
4019:Inhibitors:
3954:Inhibitors:
3828:Inhibitors:
3780:Tryptamines
3728:Inhibitors:
3663:Epinephrine
3597:Inhibitors:
3527:Inhibitors:
3475:Aquayamycin
3457:Inhibitors:
3414:Inhibitors:
3371:epinephrine
3261:Adarigiline
3255:Inhibitors:
3222:Moclobemide
3151:Brofaromine
3146:Befloxatone
3141:Bazinaprine
3130:Inhibitors:
3037:Iproclozide
3027:Hydralazine
2996:Inhibitors:
2918:Tooltip ALR
2855:Benserazide
2852:Inhibitors:
2692:from market
2666:Sotatercept
2654:Ambrisentan
2574:antagonists
2442:Deserpidine
2378:Pentolinium
2341:Rilmenidine
2297:Guanazodine
2277:Bethanidine
2259:Tiamenidine
2249:Guanoxabenz
1699:StatPearls
1175:epinephrine
1079:tachycardia
1056:Elimination
1004:100.010.477
850:Identifiers
691:Other names
682:Trade names
456:Properties
238:100.010.477
4177:Categories
4042:Quinacrine
3977:Naringenin
3972:Meciadanol
3943:-Histidine
3817:Tryptophan
3751:Nitecapone
3741:Entacapone
3600:CGS-19281A
3550:Nepicastat
3535:Disulfiram
3530:Bupicomide
3485:Metirosine
3333:-Deprenyl)
3324:Safinamide
3319:Rasagiline
3304:Mofegiline
3299:Milacemide
3294:Lazabemide
3289:Ladostigil
3266:Almoxatone
3242:Toloxatone
3237:Tetrindole
3227:Pirlindole
3171:Eprobemide
3161:Clorgiline
3156:Cimoxatone
3136:Amiflamine
3087:Phenelzine
3082:Paraxazone
3062:Mebanazine
3042:Iproniazid
3032:Indantadol
3022:Guineesine
3007:Caroxazone
2875:Methyldopa
2845:Tryptamine
2841:Tryptophan
2811:-Histidine
2756:modulators
2753:metabolism
2662:Sitaxentan
2658:+tadalafil
2640:+tadalafil
2636:Macitentan
2596:Lidanserin
2591:Ketanserin
2528:Trimazosin
2513:Ketanserin
2475:Metirosine
2396:Peripheral
2346:Tolonidine
2336:Moxonidine
2302:Guancydine
2254:Methyldopa
2244:Guanfacine
1409:2023-10-30
1384:2023-10-30
1332:2023-10-30
1274:US 6359001
1185:References
1181:) levels.
1039:Absorption
945:ChemSpider
880:CAS Number
859:IUPAC name
746:Metyrosine
661:Metirosine
641:metirosine
594:amino-acid
551:metirosine
549:) form as
494:Molar mass
346:DOQ0J0TPF7
322:2RS:
251:IUPHAR/BPS
196:2RS:
173:ChemSpider
127:3D model (
113:2RS:
89:CAS Number
35:-tyrosine
18:Metirosine
4109:See also:
4078:Histamine
4047:SKF-91488
4037:Metoprine
4032:Harmaline
4008:Histamine
3947:Histamine
3915:Histamine
3901:Melatonin
3867:Serotonin
3790:melatonin
3786:serotonin
3766:Tolcapone
3756:Opicapone
3605:SKF-64139
3560:Tropolone
3314:Pargyline
3274:-Deprenyl
3217:Minaprine
3197:norharman
3189:harmaline
3112:Safrazine
3077:Octamoxin
3072:Nialamide
3057:Linezolid
3052:Isoniazid
2985:Serotonin
2870:Genistein
2860:Carbidopa
2832:-Tyrosine
2815:Histamine
2803:Serotonin
2750:Monoamine
2702:Phase III
2690:Withdrawn
2650:selective
2644:Riociguat
2518:Indoramin
2508:Doxazosin
2452:Reserpine
2419:Pargyline
2312:Guanoclor
2292:Guanadrel
2282:Bretylium
2239:Guanabenz
2234:Clonidine
2020:McCann UD
1973:McCann UD
1582:0009-7330
1306:15 August
1133:Mechanism
1048:Half-life
840:half-life
757:Pregnancy
713:Drugs.com
531:-tyrosine
527:α-Methyl-
373:2S:
343:2S:
314:2R:
306:2S:
280:2S:
259:2S:
217:2S:
188:2R:
180:2S:
159:2S:
138:2S:
105:2R:
97:2S:
79:-tyrosine
57:Compounds
31:α-Methyl-
4167:Medicine
3957:Catechin
3831:AGN-2979
3636:Dopamine
3610:SKF-7698
3540:Dopastin
3516:Dopamine
3490:Oudenone
3443:Tyrosine
3407:Tyrosine
3367:dopamine
3309:Nicotine
3176:Esuprone
3002:Benmoxin
2967:Dopamine
2836:Tyramine
2794:Dopamine
2632:Bosentan
2533:Urapidil
2523:Prazosin
2403:Indirect
2329:agonists
2317:Guanoxan
2124:11390253
1959:24850438
1951:17318507
1915:19723785
1866:18088364
1810:11181904
1751:10927994
1707:36944004
1631:29353821
1590:83701035
1478:46982584
1260:17308229
1171:dopamine
1163:dopamine
1155:tyrosine
1075:headache
925:DrugBank
889:672-87-7
775:ATC code
759:category
741:DailyMed
606:hydrogen
598:proteins
590:tyrosine
571:tyrosine
210:DrugBank
116:658-48-0
108:672-86-6
100:672-87-7
4193:Phenols
4052:Tacrine
3284:Ethanol
3185:harmine
3183:(e.g.,
2214:Central
2088:4613321
2050:8526970
2003:8099791
1906:2875882
1857:2668123
1680:7179194
1536:5637145
1470:7009139
1403:PubChem
1378:PubChem
1326:PubChem
934:DB00765
900:PubChem
791:)
785: (
783:C02KB01
743::
625:racemic
553:, is a
499:195.218
295:PubChem
220:DB00765
4153:Portal
3193:harman
2989:5-HIAA
2685:WHO-EM
2572:Other
2488:Direct
2122:
2086:
2048:
2001:
1957:
1949:
1913:
1903:
1864:
1854:
1808:
1749:
1705:
1678:
1671:459390
1668:
1650:Thorax
1629:
1588:
1580:
1534:
1527:297204
1524:
1476:
1468:
1356:
1284:
1258:
1214:
1159:L-DOPA
1083:tremor
954:390103
914:441350
820:℞-only
818:
739:
686:Demser
602:methyl
567:serine
543:chiral
440:SMILES
309:441350
283:D00762
183:390103
152:ChEMBL
3852:AANAT
3821:5-HTP
3676:MOPEG
3672:DOPEG
3645:DOPAC
2971:DOPAC
2799:5-HTP
2608:(for
1955:S2CID
1586:S2CID
1474:S2CID
1450:Drugs
1145:As a
592:, an
395:InChI
317:12650
191:12129
129:JSmol
3993:HNMT
3882:ASMT
3681:DOMA
3621:COMT
3571:PNMT
2958:MHPG
2949:DHMA
2936:MHPG
2927:DHMA
2905:ALDH
2865:DFMD
2772:AAAD
2624:dual
2141:and
2120:PMID
2084:PMID
2046:PMID
1999:PMID
1947:PMID
1911:PMID
1862:PMID
1806:PMID
1747:PMID
1703:PMID
1676:PMID
1627:PMID
1578:ISSN
1532:PMID
1466:PMID
1354:ISBN
1308:2020
1256:PMID
1212:ISBN
1177:and
832:data
709:AHFS
696:USAN
631:and
535:AMPT
336:UNII
325:3125
273:KEGG
262:6956
199:3013
4063:DAO
3925:HDC
3802:TPH
3685:VMA
3501:DBH
3388:PAH
2980:HVA
2962:VMA
2940:VMA
2914:ALR
2886:MAO
2660:),
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