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the synthesis of GABA . In response to abiotic stresses, GABA is also reported to be synthesized from proline via D1-pyrroline intermediate formation and also by a nonenzymatic reaction . However, GABA synthesis from polyamine pathways is minor in the brain, although they play a significant role in the developing brain and retina . But GABA can be formed from putrescine in the mammalian brain .
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Alternate pathways of GABA synthesis from putrescine and other polyamines have also been reported . Here, γ-aminobutyraldehyde, an intermediate from polyamine degradation reaction via combined activities of diamine oxidase (DAO, E.C. 1.4.3.6) and 4-aminobutyraldehyde dehydrogenase (ABALDH), leads to
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In biological mixtures γ-aminobutyraldehyde may be alternatively oxidized by aldehyde dehydrogenases (EC 1.2.1.3) to γ-aminobutyric acid (GABA) (11—13). The formation of 4-amino-1-butanol is also possible through reduction by aldehyde dehydrogenase and/or alcohol dehydrogenase (13,14), thus
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preventing cyclization. Other fates of putrescine in biological mixtures include the acetylation to acetylputrescine by an N-acetyltransferase and then oxidation by monoamine oxidase (EC 1.4.3.4) (11,17). Fig 1 Fates of putrescine in biological mixtures
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Shelp BJ, Bozzo GG, Trobacher CP, Zarei A, Deyman KL, Brikis CJ (September 2012). "Hypothesis/review: contribution of putrescine to 4-aminobutyrate (GABA) production in response to abiotic stress".
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MAO also catalyses the deamination of a natural brain constituent, monoacetyl-putrescine, producing y-acetylaminobutyraldehyde, which in turn participates in the formation of brain GABA .
2313:
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Rashmi, Deo; Zanan, Rahul; John, Sheeba; Khandagale, Kiran; Nadaf, Altafhusain (2018). "γ-Aminobutyric Acid (GABA): Biosynthesis, Role, Commercial
Production, and Applications".
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Takahashi H, Uchikura K, Takahashi H (June 1961). "Relationship between pharmacological actions on the mammalian ileum and chemical structure of gamma-aminobutyric acid".
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Takahashi H, Koshino C, Ikeda O (February 1962). "Relationship between the hypotensive activity and chemical structure of gamma-aminobutyric acid in the rabbit".
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413:(GABAL). Similar to the conversion of 1,4-BD into GHB, 4-amino-1-butanol is converted into GABAL by
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Benedetti MS, Dostert P (1994). "Contribution of amine oxidases to the metabolism of xenobiotics".
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Storer, R. James; Ferrante, Antonio (10 October 1997). "Radiochemical Assay of
Diamine Oxidase".
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in this pathway, whereas the analogous intermediate structure for 4-amino-1-butanol and GABA is
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469:. Methods in Molecular Biology. Vol. 79. New Jersey: Humana Press. pp. 91–96.
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389:(GHB) is analogous to the relation of 4-amino-1-butanol to GABA. 1,4-BD is a known
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585:"γ-Hydroxybutyric Acid: Pharmacokinetics, Pharmacodynamics, and Toxicology"
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637:"Current Insights on the Impact of Gamma-Hydroxybutyrate (GHB) Abuse"
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Except where otherwise noted, data are given for materials in their
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4-Amino-1-butanol; 4-Aminobutanol; 4-Hydroxybutylamine; 4-Hydroxy-
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of GHB which is converted into it through the actions of
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583:Felmlee MA, Morse BL, Morris ME (January 2021).
417:(ALR) and GABAL is converted into GABA by ALDH.
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16:Organic compound and GABA analogue and precursor
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695:. Vol. 57. Elsevier. pp. 413–452.
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2087:Tooltip γ-Aminobutyric acid A-rho receptor
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244:InChI=1S/C4H11NO/c5-3-1-2-4-6/h6H,1-5H2
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2412:Tooltip γ-Aminobutyric acid B receptor
870:Tooltip γ-Aminobutyric acid A receptor
137:
692:Studies in Natural Products Chemistry
247:Key: BLFRQYKZFKYQLO-UHFFFAOYSA-N
7:
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2717:GABA metabolism/transport modulators
1113:Positive modulators (abridged; see
177:
701:10.1016/b978-0-444-64057-4.00013-2
14:
2648:Homotaurine (tramiprosate, 3-APS)
2146:-Chloroacetylcytosine arabinoside
941:Homotaurine (tramiprosate, 3-APS)
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635:Tay E, Lo WK, Murnion B (2022).
301:
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1940:Pentylenetetrazol (pentetrazol)
329:(at 25 °C , 100 kPa).
749:10.1016/j.plantsci.2012.06.001
304:
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1:
2699:Receptor/signaling modulators
1854:Isopregnanolone (sepranolone)
2752:. You can help Knowledge by
2710:receptor positive modulators
1218:ergoloid (dihydroergotoxine)
2819:Neurotransmitter precursors
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1909:Nonsteroidal antiandrogens
601:10.1208/s12248-020-00543-z
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1458:sulfonmethane (sulfonal)
524:10.2170/jjphysiol.11.229
475:10.1385/0-89603-448-8:91
559:10.2170/jjphysiol.12.97
2829:Organic compound stubs
2814:GABA receptor agonists
2744:This article about an
2337:5α-Dihydroprogesterone
1884:Morphine-3-glucuronide
1544:Hyenachin (mellitoxin)
1429:Retigabine (ezogabine)
403:γ-Hydroxybutyraldehyde
399:aldehyde dehydrogenase
59:-(4-Hydroxybutyl)amine
1725:Chlorophenylsilatrane
395:alcohol dehydrogenase
387:γ-hydroxybutyric acid
2675:Negative modulators:
2555:Positive modulators:
2448:Arbaclofen placarbil
2334:Negative modulators:
2183:Positive modulators:
1968:Pregnenolone sulfate
1604:17-Phenylandrostenol
1586:Negative modulators:
1471:constituents (e.g.,
1441:constituents (e.g.,
1303:Neuroactive steroids
1280:constituents (e.g.,
1016:Neuroactive steroids
735:. 193–194: 130–135.
411:γ-aminobutyraldehyde
2264:Gabazine (SR-95531)
2254:CGP-36742 (SGS-742)
1962:dihydropicrotoxinin
1687:Bicyclic phosphates
1599:11-Ketoprogesterone
1534:Gabazine (SR-95531)
1359:pyrazolopyrimidines
741:2012PlnSc.193..130S
654:10.2147/SAR.S315720
641:Subst Abuse Rehabil
467:Polyamine Protocols
438:"4-Amino-1-butanol"
372:γ-aminobutyric acid
353:4-hydroxybutylamine
319: g·mol
21:
1785:FG-7142 (ZK-31906)
1331:Nonbenzodiazepines
415:aldehyde reductase
333:Infobox references
20:4-Amino-1-butanol
19:
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2279:Isonipecotic acid
1644:Anabolic steroids
1614:α5IA (LS-193,268)
1524:Dihydrosecurinine
1409:Pyrazolopyridines
1178:potassium bromide
1176:compounds (e.g.,
1139:Anabolic steroids
1117:for a full list):
971:Isonipecotic acid
710:978-0-444-64057-4
484:978-0-89603-448-8
345:4-Amino-1-butanol
341:Chemical compound
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200:CompTox Dashboard
106:Interactive image
43:4-aminobutan-1-ol
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1574:Thiocolchicoside
1394:Piperidinediones
1351:imidazopyridines
1307:allopregnanolone
1214:Dihydroergolines
1129:drinking alcohol
1020:allopregnanolone
936:Gaboxadol (THIP)
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2649:
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2599:
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2446:
2444:
2441:
2439:
2438:Aceburic acid
2436:
2434:
2431:
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2426:
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2418:
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2154:
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2149:
2147:
2145:
2141:
2139:
2136:
2134:
2131:
2129:
2128:Ibotenic acid
2126:
2124:
2121:
2119:
2116:
2114:
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2109:
2106:
2104:
2101:
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2011:
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2006:
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1973:Propybicyphat
1971:
1969:
1966:
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1959:
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1935:Oenanthotoxin
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1926:
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1900:
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1867:
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1862:
1860:
1857:
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1847:
1845:
1844:Iomazenil (I)
1842:
1840:
1837:
1835:
1832:
1830:
1827:
1824:
1823:ciprofloxacin
1820:
1817:
1815:
1812:
1809:
1805:
1804:amentoflavone
1801:
1798:
1795:
1791:
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1786:
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1778:
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1768:
1766:
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1758:
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1753:
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1748:
1746:
1743:
1741:
1740:Cyclothiazide
1738:
1736:
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1731:
1728:
1726:
1723:
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1718:
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1547:
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1540:
1537:
1535:
1532:
1530:
1529:Famiraprinium
1527:
1525:
1522:
1520:
1517:
1515:
1512:
1509:
1508:
1504:
1500:
1496:
1495:diethyl ether
1492:
1488:
1484:
1480:
1477:
1474:
1470:
1467:
1465:
1462:
1459:
1455:
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1407:
1405:
1402:
1399:
1395:
1392:
1390:
1387:
1384:
1380:
1377:
1375:
1372:
1370:
1369:Norfluoxetine
1367:
1364:
1360:
1356:
1352:
1348:
1344:
1340:
1336:
1332:
1329:
1327:
1324:
1322:
1319:
1316:
1312:
1308:
1304:
1301:
1299:
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1256:
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1249:
1245:
1242:
1239:
1235:
1232:
1230:
1227:
1225:
1222:
1219:
1215:
1212:
1210:
1209:Clomethiazole
1207:
1205:
1204:Chlormezanone
1202:
1200:
1197:
1195:
1194:Carbamazepine
1192:
1189:
1185:
1182:
1179:
1175:
1172:
1169:
1165:
1162:
1159:
1158:phenobarbital
1155:
1152:
1149:
1145:
1142:
1140:
1137:
1134:
1130:
1126:
1123:
1121:
1118:
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1107:
1104:
1102:
1099:
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1087:
1084:
1082:
1079:
1077:
1074:
1072:
1069:
1067:
1064:
1062:
1061:Quisqualamine
1059:
1057:
1054:
1052:
1049:
1047:
1044:
1042:
1039:
1037:
1034:
1032:
1029:
1027:
1024:
1021:
1017:
1014:
1012:
1009:
1007:
1004:
1002:
999:
997:
996:Methylglyoxal
994:
991:
987:
984:
982:
979:
977:
974:
972:
969:
967:
964:
962:
959:
957:
954:
952:
949:
947:
946:Ibotenic acid
944:
942:
939:
937:
934:
932:
929:
927:
924:
922:
919:
917:
914:
912:
909:
907:
904:
902:
899:
896:
895:phenobarbital
892:
889:
887:
884:
882:
879:
876:
875:
873:
868:
859:
856:
854:
850:
846:
843:
833:
828:
826:
821:
819:
814:
813:
810:
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796:
792:
788:
784:
780:
776:
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767:
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750:
746:
742:
738:
734:
727:
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702:
698:
694:
693:
685:
683:
679:
674:
670:
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631:
629:
625:
620:
616:
611:
606:
602:
598:
594:
590:
586:
579:
577:
573:
568:
564:
560:
556:
552:
548:
547:Jpn J Physiol
541:
538:
533:
529:
525:
521:
517:
513:
512:Jpn J Physiol
506:
503:
499:
494:
490:
486:
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468:
461:
459:
455:
443:
439:
433:
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404:
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396:
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375:
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328:
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315:
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310:
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288:
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266:
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201:
197:
196:
189:
185:
184:
182:
176:
172:
171:
164:
163:
161:
159:
154:
153:
149:
145:
142:
140:
138:ECHA InfoCard
135:
134:
127:
123:
122:
120:
118:
115:
114:
107:
103:
102:
100:
96:
91:
90:
83:
79:
78:
76:
73:
69:
68:
63:
58:
55:-butylamine;
54:
47:
41:
37:
32:
28:
23:
2754:expanding it
2743:
2728:
2715:
2704:
2697:
2674:
2605:Antagonists:
2604:
2554:
2419:
2395:Metabotropic
2366:Pregnanolone
2360:picrotoxinin
2333:
2319:
2246:
2216:(S)-4-ACPBPA
2211:(S)-2-MeGABA
2208:Antagonists:
2207:
2182:
2171:Thiomuscimol
2143:
2094:
1958:picrotoxinin
1921:enzalutamide
1917:bicalutamide
1839:Golexanolone
1735:Cloflubicyne
1585:
1511:Antagonists:
1510:
1423:methaqualone
1398:glutethimide
1374:Petrichloral
1335:β-carbolines
1154:Barbiturates
1112:
1096:Thiomuscimol
901:Beta-Alanine
891:Barbiturates
881:(+)-Catechin
877:
798:
778:
774:
732:
714:
691:
644:
640:
592:
588:
550:
546:
540:
515:
511:
505:
496:
466:
445:. Retrieved
441:
407:intermediate
385:(1,4-BD) to
381:relation of
376:
357:alkanolamine
352:
348:
344:
343:
65:Identifiers
56:
52:
49:Other names
2678:Compound 14
2508:Lesogaberan
2347:Loreclezole
2284:Loreclezole
2221:(S)-4-ACPCA
2201:Lanthanides
2191:Alphaxolone
2133:Isoguvacine
2043:Terbequinil
1913:apalutamide
1904:Nicardipine
1864:Laudanosine
1671:carbapenems
1663:penicillins
1519:Coriamyrtin
1514:Bicuculline
1503:sevoflurane
1499:paraldehyde
1449:Stiripentol
1326:Niacinamide
1311:cholesterol
1293:Loreclezole
1188:meprobamate
1144:Avermectins
1011:Nefiracetam
976:Kojic amine
966:Isomuscimol
961:Isoguvacine
447:8 September
277:Properties
144:100.033.045
2793:Categories
2533:SKF-97,541
2443:Arbaclofen
2352:Picrotoxin
2342:Bilobalide
2018:Suritozole
2008:Sarmazenil
1993:Ro 19-4603
1988:Ro 15-4513
1983:Radequinil
1950:Picrotoxin
1929:nilutamide
1899:Naltrexone
1834:Furosemide
1814:Flumazenil
1808:oroxylin A
1800:Flavonoids
1780:Etbicyphat
1710:Bilobalide
1677:Basmisanil
1564:Sinomenine
1559:Securinine
1554:Pitrazepin
1539:Hydrastine
1491:chloroform
1464:Topiramate
1404:Propanidid
1268:Imidazoles
1263:Flupirtine
1258:Fluoxetine
1252:hispidulin
1244:Flavonoids
1199:Chloralose
1184:Carbamates
1148:ivermectin
1086:Terpenoids
1031:PF-6372865
886:Bamaluzole
853:Ionotropic
845:modulators
553:: 97–105.
421:References
397:(ADH) and
379:structural
312:Molar mass
117:ChemSpider
93:3D model (
82:13325-10-5
72:CAS Number
40:IUPAC name
2668:SKF-97541
2663:SCH-50911
2653:Phaclofen
2638:CGP-64213
2633:CGP-55845
2628:CGP-54626
2623:CGP-52432
2618:CGP-46381
2613:CGP-35348
2583:CGP-13501
2558:ADX-71441
2543:Tolgabide
2523:Progabide
2518:Picamilon
2503:Isovaline
2420:Agonists:
2322:-3-ACPBPA
2299:SKF-97541
2249:-3-ACPBPA
2176:Tolgabide
2156:Progabide
2151:Picamilon
2095:Agonists:
2003:RO4938581
1998:RO4882224
1925:flutamide
1859:L-655,708
1829:Flurothyl
1730:Cicutoxin
1715:Bupropion
1682:Bemegride
1659:β-Lactams
1649:Amiloride
1479:Volatiles
1413:etazolate
1389:Phenytoin
1347:zopiclone
1339:abecarnil
1298:Monastrol
1288:Lanthanum
1272:etomidate
1234:Fenamates
1229:Etifoxine
1224:Etazepine
1101:Tolgabide
1051:Progabide
1041:Picamilon
1026:Org 20599
1001:Monastrol
981:L-838,417
878:Agonists:
733:Plant Sci
647:: 13–23.
595:(1): 22.
365:precursor
165:236-364-4
157:EC Number
2824:Prodrugs
2799:Alcohols
2694:See also
2658:Saclofen
2593:rac-BHFF
2588:GS-39783
2578:CGP-7930
2538:SL 75102
2513:Phenibut
2468:Gabamide
2453:Baclofen
2356:picrotin
2309:SR-95813
2304:SR-95318
2226:2-MeTACA
2138:Muscimol
2068:ZK-93426
2038:TCS-1105
2023:TB-21007
1954:picrotin
1894:Naloxone
1879:Morphine
1874:MaxiPost
1794:fipronil
1790:Fiproles
1760:(+)-DMBB
1755:Dieldrin
1654:Anisatin
1569:SR-42641
1469:Valerian
1443:baicalin
1439:Skullcap
1383:propofol
1363:zaleplon
1355:zolpidem
1248:apigenin
1168:diazepam
1125:Alcohols
1066:SL-75102
1056:Propofol
1036:Phenibut
1006:Muscimol
990:honokiol
956:iso-THIP
951:iso-THAZ
926:Gabamide
842:receptor
757:22794926
673:35173515
619:33417072
567:13919036
532:13774871
401:(ALDH).
374:(GABA).
361:analogue
355:, is an
268:C(CCO)CN
2563:BHF-177
2548:Tolibut
2458:BL-1020
2371:ROD-188
2236:4-ACPAM
2231:3-APMPA
2098:BL-1020
2058:U-93631
2053:Thujone
1978:PWZ-029
1952:(i.e.,
1911:(e.g.,
1889:MRK-016
1869:Lindane
1821:(e.g.,
1802:(e.g.,
1792:(e.g.,
1661:(e.g.,
1639:β-EMGBL
1549:PHP-501
1485:(e.g.,
1456:(e.g.,
1434:ROD-188
1421:(e.g.,
1411:(e.g.,
1396:(e.g.,
1381:(e.g.,
1379:Phenols
1361:(e.g.,
1353:(e.g.,
1345:(e.g.,
1337:(e.g.,
1333:(e.g.,
1305:(e.g.,
1270:(e.g.,
1246:(e.g.,
1236:(e.g.,
1216:(e.g.,
1186:(e.g.,
1174:Bromide
1166:(e.g.,
1156:(e.g.,
1146:(e.g.,
1127:(e.g.,
1120:α-EMTBL
1090:borneol
1088:(e.g.,
1071:Taurine
1018:(e.g.,
988:(e.g.,
986:Lignans
906:BL-1020
893:(e.g.,
795:7924902
737:Bibcode
664:8843350
610:8098080
493:9463822
442:PubChem
391:prodrug
367:of the
359:and an
175:PubChem
2804:Amines
2598:KK-92A
2428:3-APPA
2196:ATHDOC
1750:DHEA-S
1589:1,3M1B
1321:Niacin
1282:kavain
793:
755:
707:
671:
661:
617:
607:
589:AAPS J
565:
530:
491:
481:
317:89.138
261:SMILES
34:Names
2748:is a
2488:GHBAL
2473:GABOB
2376:THDOC
2320:trans
2314:TPMPA
2289:P4MPA
2241:4-GBA
2123:GABOB
1849:IPTBO
1699:IPTBO
1634:β-CCP
1629:β-CCM
1624:β-CCE
1619:β-CCB
1579:Tutin
1483:gases
1315:THDOC
931:GABOB
347:, or
236:InChI
188:25868
126:24099
95:JSmol
2750:stub
2706:GABA
2643:DAVA
2573:BSPP
2568:BHFF
2463:GABA
2405:GABA
2381:Zinc
2327:ZAPA
2274:I4AA
2259:DAVA
2166:TAMP
2161:TACA
2118:GABA
2108:CAMP
2103:CACA
2079:GABA
2063:Zinc
2048:TETS
2033:TBPS
2028:TBOB
1960:and
1775:EBOB
1770:DMPC
1765:DMCM
1745:DHEA
1720:CHEB
1705:BIDN
1695:TBPO
1691:TBPS
1609:α3IA
1594:3M2B
1278:Kava
1133:2M2B
1115:here
1106:ZAPA
1081:TAMP
1076:TACA
921:GABA
911:DAVA
863:GABA
840:GABA
791:PMID
753:PMID
705:ISBN
669:PMID
615:PMID
563:PMID
528:PMID
489:PMID
479:ISBN
449:2024
377:The
363:and
2498:GVL
2493:GHV
2483:GHB
2478:GBL
2294:P4S
2247:cis
2013:SCS
1357:),
1349:),
1341:),
1046:P4S
783:doi
745:doi
697:doi
659:PMC
649:doi
605:PMC
597:doi
555:doi
520:doi
471:doi
205:EPA
178:CID
2795::
2358:,
2083:-ρ
1956:,
1927:,
1923:,
1919:,
1915:,
1806:,
1697:,
1693:,
1669:,
1665:,
1501:,
1497:,
1493:,
1489:,
1365:))
1313:,
1309:,
1250:,
1131:,
797:.
789:.
779:26
777:.
765:^
751:.
743:.
723:^
713:.
703:.
681:^
667:.
657:.
645:13
643:.
639:.
627:^
613:.
603:.
593:23
591:.
587:.
575:^
561:.
551:12
549:.
526:.
516:11
514:.
495:.
487:.
477:.
457:^
440:.
429:^
299:11
2781:e
2774:t
2767:v
2756:.
2708:A
2407:B
2362:)
2354:(
2144:N
2081:A
1964:)
1931:)
1825:)
1810:)
1796:)
1701:)
1689:(
1673:)
1505:)
1481:/
1475:)
1460:)
1445:)
1425:)
1415:)
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865:A
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305:O
302:N
296:H
293:4
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57:N
53:n
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