Diampromide

Diampromide
Clinical data
Other names	Diampromide
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class A1 (Narcotic drugs); 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 ;
ChemSpider	56158 ;
UNII	26G7YC77BU;
KEGG	D12694 ;
ChEMBL	ChEMBL2106220;
CompTox Dashboard (EPA)	DTXSID70862177 ;
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 ; Key:RXTHKWVSXOIHJS-UHFFFAOYSA-N ;
	(verify)

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,^[2] and can be described as a ring-opened analogue of fentanyl.^[3]

Diampromide produces similar effects to other opioids, including analgesia, sedation, dizziness and nausea, and is around the same potency as morphine.^[4]

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.^[5] 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.

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ US 2944081, "Diphenylalkylenediamines and Methods of Preparation of the Same"
^ "Theoretical Study of Acyclic FENTANYL ANALOGS With Analgesic Activity: Diampromide and seco-Fentanyl".
^ 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.
^ "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.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] US 2944081, "Diphenylalkylenediamines and Methods of Preparation of the Same"

[3] "Theoretical Study of Acyclic FENTANYL ANALOGS With Analgesic Activity: Diampromide and seco-Fentanyl".

[4] 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.

[5] "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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