2-MDP

2-MDP
Identifiers
IUPAC name
  • 3-amino-2-methyl-1,1-di(phenyl)propan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H19NO
Molar mass241.334 g·mol−1
3D model (JSmol)
SMILES
  • OC(c1ccccc1)(c2ccccc2)C(C)CN
InChI
  • InChI=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 checkY
  • Key:XGYCHIPEPHYUIH-UHFFFAOYSA-N checkY
 ☒NcheckY (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

The therapeutic action is said to exhibit appetite suppressant and antidepressant[4] like activity.

Synthesis

2-MDP Synthesis:[5]

In a variation of the nitrile-Aldol reaction (also demonstrated for venlafaxine), 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 [6275-86-1] (3). The reduction of the intermediate nitrile group with lithium aluminium hydride completed the synthesis of U-23,807A (4).

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.


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