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

File:AL-1095 synthesis.svg

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.

See also

References