:2-MDP

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477213709

| IUPAC_name = 3-amino-2-methyl-1,1-di(phenyl)propan-1-ol

| image = 2-MDP.svg

| width = 150

| tradename =

| legal_status =

| routes_of_administration =

| metabolism =

| elimination_half-life =

| excretion =

| index2_label = HCl

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 14326-31-9

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 14185-05-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = B6FTK35FGC

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = TJH732RKT9

| PubChem = 26538

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 24719

| C=16 | H=19 | N=1 | O=1

| smiles = OC(c1ccccc1)(c2ccccc2)C(C)CN

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C16H19NO/c1-13(12-17)16(18,14-8-4-2-5-9-14)15-10-6-3-7-11-15/h2-11,13,18H,12,17H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XGYCHIPEPHYUIH-UHFFFAOYSA-N

}}

2-MDP (U-23807A) is a dissociative anaesthetic drug which has been found to be an NMDA antagonist and produces similar effects to PCP in animals. The levo or (−)-isomer is the active form of the drug.{{cite journal | vauthors = Tang AH, Cangelosi AA, Code RA, Franklin SR | title = Phencyclidine-like behavioral effects of 2-methyl-3,3-diphenyl-3-propanolamine (2-MDP) | journal = Pharmacology, Biochemistry, and Behavior | volume = 20 | issue = 2 | pages = 209–213 | date = February 1984 | pmid = 6718449 | doi = 10.1016/0091-3057(84)90244-2 | s2cid = 38908019 }}{{cite journal | vauthors = Blake JC, Davies SN, Church J, Martin D, Lodge D | title = 2-Methyl-3,3-diphenyl-3-propanolamine (2-MDP) selectively antagonises N-methyl-aspartate (NMA) | journal = Pharmacology, Biochemistry, and Behavior | volume = 24 | issue = 1 | pages = 23–25 | date = January 1986 | pmid = 3511477 | doi = 10.1016/0091-3057(86)90038-9 | s2cid = 29762524 }} It also has stimulant effects, having only around one third the potency of amphetamine by weight, but with a long duration of action, lasting more than 24 hours from a single oral dose.{{cite journal | vauthors = Biel JH | title = Antidepressants, Stimulants, Hallucinogens. | veditors = Cain CK | journal = Annual Reports in Medicinal Chemistry | date = January 1967 | volume = 2 | pages = 11–23, 18 | publisher = Academic Press | doi = 10.1016/S0065-7743(08)61499-2 }}

Effects

The therapeutic action is said to exhibit appetite suppressant- and antidepressant-like activity.{{cite journal | vauthors = Shipley GS, Bishop MP, Gallant DM | title = A controlled evaluation of U-23,807A in the neurotic depressive syndrome | journal = Current Therapeutic Research, Clinical and Experimental | volume = 9 | issue = 10 | pages = 514–516 | date = October 1967 | pmid = 4964946 }}

Synthesis

File:U-23,807A synthesis.svg

In a variation of the nitrile-aldol reaction, combination of benzophenone (1) and propionitrile (2), in the presence of sodamide base and ethyl ether solvent, leads to 3-hydroxy-2-methyl-3,3-diphenylpropanenitrile (3).{{cite journal | vauthors = Moffett RB, Pickering TL | title = Central nervous system agents. 2. Synthesis of diphenyl primary and secondary aminopropanols | journal = Journal of Medicinal Chemistry | volume = 14 | issue = 11 | pages = 1100–1106 | date = November 1971 | pmid = 5115211 | doi = 10.1021/jm00293a019 }} The reduction of the intermediate nitrile group with lithium aluminium hydride completes the synthesis of 2-MDP (4).

References

{{Reflist}}

{{Hallucinogens}}

{{Stimulants}}

{{Ionotropic glutamate receptor modulators}}

Category:Dissociative drugs

Category:Stimulants