AL-1095
{{Short description|Stimulant drug}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477235632
| IUPAC_name = 2-(1-phenyl-1-(p-chlorophenyl)methyl)-3-hydroxyquinuclidine
| image = AL-1095 Structure.svg
| tradename =
| pregnancy_category =
| legal_status = Unscheduled
| routes_of_administration =
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 54549-19-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FBM6V6H8CK
| ATC_prefix = none
| ATC_suffix =
| PubChem = 3041659
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2304906
| C=20 | H=22 | Cl=1 | N=1 | O=1
| smiles = OC(C1CCN2CC1)C2C(C3=CC=C(Cl)C=C3)C4=CC=CC=C4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H22ClNO/c21-17-8-6-15(7-9-17)18(14-4-2-1-3-5-14)19-20(23)16-10-12-22(19)13-11-16/h1-9,16,18-20,23H,10-13H2/t18?,19-,20+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JXCMZYHEZWCLOD-NRRUETGQSA-N
}}
AL-1095,{{cite patent | country = US | number = 3506673 | title = 2-(4'Halo)-Benzhydryl-3-Quinuclidinols | gdate = 14 April 1970 | inventor = Warawa ED, Mueller NJ | assign1 = Aldrich Chemical Company }} is a centrally acting stimulant drug with comparable effects to amphetamine,{{cite book | vauthors = Hedblom P, Grinspoon L | title = The Speed Culture: Amphetamine Use and Abuse in America | publisher = Harvard University Press | location = Cambridge | year = 1975 | page = [https://archive.org/details/speedcultureamph0000grin_n3i0/page/50 50] | isbn = 0-674-83192-6 | url = https://archive.org/details/speedcultureamph0000grin_n3i0 | url-access = registration }} developed by Bristol in the 1970s.{{cite journal | vauthors = Warawa EJ, Mueller NJ | title = Quinuclidine Chemistry. 3. β-cis-2-(4'-Chlorobenzhydryl)-3-quinuclidinol, a New Central Nervous System Stimulant. Importance of the Benzhydryl Configuration | journal = Journal of Medicinal Chemistry | volume = 18 | issue = 1 | pages = 71–4 | date = January 1975 | pmid = 803245 | doi = 10.1021/jm00235a016 }}
Synthesis
The first-step is a mixed-aldol condensation between 3-quinuclidinone [3731-38-2] (1) and benzaldehyde (2) gives 2-benzylidene-3-oxoquinuclidine [24123-89-5] (3). The conjugate addition of the Grignard reagent formed from 4-bromochlorobenzene [106-39-8] (4) to the enone gives the benzhydryl (5). MPV reduction of the carbonyl gives the syn stereoisomers, whereas borohydride gave trans. Both diastereoisomers are active but in only one of the enantiomers.