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2-MDP

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
2-MDP
Identifiers
  • 3-amino-2-methyl-1,1-di(phenyl)propan-1-ol
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC16H19NO
Molar mass241.334 g·mol−1
3D model (JSmol)
  • OC(c1ccccc1)(c2ccccc2)C(C)CN
  • 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 adissociativeanaesthetic drug which has been found to be anNMDA antagonist and produces similar effects toPCP in animals. Thelevo or (−)-isomer is the active form of the drug.[1][2] It also hasstimulant effects, having only around one third the potency ofamphetamine 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]
2-MDP synthesis

In a variation of the nitrile-aldol reaction, combination ofbenzophenone (1) andpropionitrile (2), in the presence ofsodamide base andethyl ether solvent, leads to 3-hydroxy-2-methyl-3,3-diphenylpropanenitrile (3).[5] The reduction of the intermediate nitrile group withlithium aluminium hydride completes the synthesis of 2-MDP (4).

References

[edit]
  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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