| 词条 | Lysergic acid 2-butyl amide |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 419986581 | IUPAC_name = (8β)-6-Methyl-N-[(1R)-1-methylpropyl]-9,10-didehydroergoline-8-carboxamide | image = SBULSD.svg | width = 140 | tradename = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | metabolism = | excretion = | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 137765-82-3 | CAS_supplemental = (R,R) isomer, freebase 137765-83-4 (R,R) isomer, maleate salt | PubChem = 15119692 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 23157987 | C=20 | H=25 | N=3 | O=1 | molecular_weight = 323.431 g/mol | smiles = CN1C[C@@H](C(N[C@H](C)CC)=O)C=C2C1CC3=CNC4=C3C2=CC=C4 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C20H25N3O/c1-4-12(2)22-20(24)14-8-16-15-6-5-7-17-19(15)13(10-21-17)9-18(16)23(3)11-14/h5-8,10,12,14,18,21H,4,9,11H2,1-3H3,(H,22,24)/t12-,14-,18-/m1/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = NYFSQPDQLFFBRA-RVZJWNSFSA-N | synonyms = (6aR,9R)- N- (R)- 2-butyl- 7-methyl- 4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide }} Lysergic acid 2-butyl amide (2-Butyllysergamide, LSB) is an analogue of LSD originally developed by Richard Pioch at Eli Lilly in the 1950s,[1] but mostly publicised through research conducted by the team led by David E. Nichols at Purdue University. It is a structural isomer of LSD, with the two ethyl groups on the amide nitrogen having been replaced by a single sec-butyl group, joined at the 2-position.[2] It is one of the few lysergamide derivatives to exceed the potency of LSD in animal drug discrimination assays, with the (R) isomer having an ED50 of 33nmol/kg for producing drug-appropriate responding, vs 48nmol/kg for LSD itself. The corresponding (R)-2-pentyl analogue has higher binding affinity for the 5-HT1A and 5-HT2A receptors, but is less potent in producing drug-appropriate responding, suggesting that the butyl compound has a higher efficacy at the receptor target.[3] The drug discrimination assay for LSD in rats involves both 5-HT1A and 5-HT2A mediated components, and while lysergic acid 2-butyl amide is more potent than LSD as a 5-HT1A agonist, it is slightly less potent as a 5-HT2A agonist, and so would probably be slightly less potent than LSD as a hallucinogen in humans. The main use for this drug has been in studies of the binding site at the 5-HT2A receptor through which LSD exerts most of its pharmacological effects,[4] with the stereoselective activity of these unsymmetric monoalkyl lysergamides foreshadowing the subsequent development of compounds such as lysergic acid 2,4-dimethylazetidide (LSZ). See also
References1. ^{{ cite patent | country = US | number = 2997470 | status = patent | title = LYSERGIC ACID AMIDES | pubdate = 1956-03-05 | gdate = 1961-08-22 | inventor = Richard P. Pioch}} {{Hallucinogenic lysergamides}}{{Serotonergics}}{{Ergolines}}2. ^Oberlender R, Pfaff RC, Johnson MP, Huang XM, Nichols DE. Stereoselective LSD-like activity in d-lysergic acid amides of (R)- and (S)-2-aminobutane. Journal of Medicinal Chemistry. 1992 Jan 24;35(2):203-11. {{PMID|1732537}} 3. ^Monte AP, Marona-Lewicka D, Kanthasamy A, Sanders-Bush E, Nichols DE. Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes. Journal of Medicinal Chemistry. 1995 Mar 17;38(6):958-66. {{DOI|10.1021/jm00006a015}} {{PMID|7699712}} 4. ^David E. Nichols. LSD and Its Lysergamide Cousins. The Heffter Review of Psychedelic Research. 2001;2:80-87. 3 : Lysergamides|Eli Lilly and Company|Designer drugs |
| 随便看 |
|
开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。