AL-1095

Stimulant drug

none

Legal statusLegal status

In general: unscheduled

Identifiers

IUPAC name

2-(1-phenyl-1-(p-chlorophenyl)methyl)-3-hydroxyquinuclidine

CAS Number

54549-19-8^Y

PubChem CID

3041659

ChemSpider

2304906^Y

UNII

FBM6V6H8CK

CompTox Dashboard (EPA)

DTXSID60969780

Chemical and physical dataFormulaC₂₀H₂₂ClNOMolar mass327.85 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

OC(C1CCN2CC1)C2C(C3=CC=C(Cl)C=C3)C4=CC=CC=C4

InChI

InChI=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^Y
Key:JXCMZYHEZWCLOD-NRRUETGQSA-N^Y

^NY (what is this?) (verify)

AL-1095,^[1] is a centrally acting stimulant drug with comparable effects to amphetamine,^[2] developed by Bristol in the 1970s.^[3]

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.

References

^ US 3506673, Warawa ED, Mueller NJ, "2-(4'Halo)-Benzhydryl-3-Quinuclidinols", issued 14 April 1970, assigned to Aldrich Chemical Company
^ Hedblom P, Grinspoon L (1975). The Speed Culture: Amphetamine Use and Abuse in America. Cambridge: Harvard University Press. p. 50. ISBN 0-674-83192-6.
^ Warawa EJ, Mueller NJ (January 1975). "Quinuclidine Chemistry. 3. β-cis-2-(4'-Chlorobenzhydryl)-3-quinuclidinol, a New Central Nervous System Stimulant. Importance of the Benzhydryl Configuration". Journal of Medicinal Chemistry. 18 (1): 71–4. doi:10.1021/jm00235a016. PMID 803245.
^ Warawa, E., Mueller, N., & Gylys, J. (1975). Additions and Corrections - Quinuclidine Chemistry. 3. β-cis-2-(4’-Chlorobenzhydryl)-3-quinuclidinol, a New Central Nervous System Stimulant. Importance of the Benzhydryl Configuration. Journal of Medicinal Chemistry, 18(12), 1275–1275. https://doi.org/10.1021/jm00246a600.