Chemistry:2-MDP

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Short description: Chemical compound
2-MDP
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H19NO
Molar mass241.334 g·mol−1
3D model (JSmol)
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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. ↑ "Phencyclidine-like behavioral effects of 2-methyl-3,3-diphenyl-3-propanolamine (2-MDP)". Pharmacology, Biochemistry, and Behavior 20 (2): 209–213. February 1984. doi:10.1016/0091-3057(84)90244-2. PMID 6718449. 
  2. ↑ "2-Methyl-3,3-diphenyl-3-propanolamine (2-MDP) selectively antagonises N-methyl-aspartate (NMA)". Pharmacology, Biochemistry, and Behavior 24 (1): 23–25. January 1986. doi:10.1016/0091-3057(86)90038-9. PMID 3511477. 
  3. ↑ "Antidepressants, Stimulants, Hallucinogens.". Annual Reports in Medicinal Chemistry (Academic Press) 2: 11–23, 18. January 1967. doi:10.1016/S0065-7743(08)61499-2. 
  4. ↑ "A controlled evaluation of U-23,807A in the neurotic depressive syndrome". Current Therapeutic Research, Clinical and Experimental 9 (10): 514–516. October 1967. PMID 4964946. 
  5. ↑ "Central nervous system agents. 2. Synthesis of diphenyl primary and secondary aminopropanols". Journal of Medicinal Chemistry 14 (11): 1100–1106. November 1971. doi:10.1021/jm00293a019. PMID 5115211. 



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