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 names	Diampromide
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	552-25-0
PubChem CID	62370
DrugBank	DB01502^Y
ChemSpider	56158^Y
UNII	26G7YC77BU
ChEMBL	ChEMBL2106220
Chemical and physical data
Formula	C21H28N2O
Molar mass	324.468 g·mol^−1
3D model (JSmol)	Interactive image
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
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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.

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.