2-MDP
 | |
| Identifiers | |
|---|---|
| |
| CAS Number |
|
| PubChem CID | |
| ChemSpider | |
| UNII |
|
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C16H19NO |
| Molar mass | 241.334 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (what is this?) (verify) | |
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.[1][2] 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.[3]
Effects
[edit]The therapeutic action is said to exhibit appetite suppressant- and antidepressant-like activity.[4]
Synthesis
[edit]
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).[5] The reduction of the intermediate nitrile group with lithium aluminium hydride completes the synthesis of 2-MDP (4).
References
[edit]- ↑ Tang AH, Cangelosi AA, Code RA, Franklin SR (February 1984). "Phencyclidine-like behavioral effects of 2-methyl-3,3-diphenyl-3-propanolamine (2-MDP)". Pharmacology, Biochemistry, and Behavior. 20 (2): 209–213. doi:10.1016/0091-3057(84)90244-2. PMID 6718449. S2CID 38908019.
- ↑ Blake JC, Davies SN, Church J, Martin D, Lodge D (January 1986). "2-Methyl-3,3-diphenyl-3-propanolamine (2-MDP) selectively antagonises N-methyl-aspartate (NMA)". Pharmacology, Biochemistry, and Behavior. 24 (1): 23–25. doi:10.1016/0091-3057(86)90038-9. PMID 3511477. S2CID 29762524.
- ↑ Biel JH (January 1967). Cain CK (ed.). "Antidepressants, Stimulants, Hallucinogens". Annual Reports in Medicinal Chemistry. 2. Academic Press: 11–23, 18. doi:10.1016/S0065-7743(08)61499-2.
- ↑ Shipley GS, Bishop MP, Gallant DM (October 1967). "A controlled evaluation of U-23,807A in the neurotic depressive syndrome". Current Therapeutic Research, Clinical and Experimental. 9 (10): 514–516. PMID 4964946.
- ↑ Moffett RB, Pickering TL (November 1971). "Central nervous system agents. 2. Synthesis of diphenyl primary and secondary aminopropanols". Journal of Medicinal Chemistry. 14 (11): 1100–1106. doi:10.1021/jm00293a019. PMID 5115211.