Diampromide

Diampromide is an opioid analgesic from the ampromide family of drugs, related to other drugs such as propiram and phenampromide. It was invented in the 1960s by American Cyanamid,[1] and can be described as a ring-opened analogue of fentanyl.[2]

Diampromide
Clinical data
Other namesDiampromide
ATC code
  • none
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule I
  • UN: Psychotropic Schedule I
Identifiers
IUPAC name
  • N-[2-(Methyl-(2-phenylethyl)amino)propyl]-N-phenylpropanamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC21H28N2O
Molar mass324.468 g·mol−1
3D model (JSmol)
SMILES
  • CCC(=O)N(CC(C)N(C)CCc1ccccc1)c1ccccc1
InChI
  • InChI=1S/C21H28N2O/c1-4-21(24)23(20-13-9-6-10-14-20)17-18(2)22(3)16-15-19-11-7-5-8-12-19/h5-14,18H,4,15-17H2,1-3H3 Y
  • Key:RXTHKWVSXOIHJS-UHFFFAOYSA-N Y
  (verify)

Diampromide produces similar effects to other opioids, including analgesia, sedation, dizziness and nausea, and is around the same potency as morphine.[3]

Diampromide is in Schedule I of the Controlled Substances Act 1970 of the United States as a Narcotic with ACSCN 9615 with a zero aggregate manufacturing quota as of 2014.[4] It is listed under the Single Convention for the Control of Narcotic Substances 1961 and is controlled in most countries in the same fashion as is morphine. It is highly poisonous.

See also

References

  1. US 2944081, "Diphenylalkylenediamines and Methods of Preparation of the Same"
  2. "Theoretical Study of Acyclic FENTANYL ANALOGS With Analgesic Activity: Diampromide and seco-Fentanyl".
  3. Ivanovic MD, Micovic IV, Vuckovic S, Prostran M, Todorovic Z, Ivanovic ER, Kiricojevic VD, Djordjevic JB, Dosen-Micovic LJ (2004). "The synthesis and pharmacological evaluation of 2,3-seco-fentanyl analogues". Journal of the Serbian Chemical Society. 69 (11): 955–968. doi:10.2298/JSC0411955I.
  4. "Final Adjusted Aggregate Production Quotas for Schedule I and II Controlled Substances and Assessment of Annual Needs for the List I Chemicals Ephedrine, Pseudoephedrine, and Phenylpropanolamine for 2014". Drug Enforcement Administration. Archived from the original on 2016-03-04. Retrieved 2016-02-26.


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