Propiram

Propiram
Clinical data
Routes of; administration	By mouth, injected
ATC code	none;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A2 (Narcotic drugs); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); US: Schedule I;
Pharmacokinetic data
Bioavailability	97%
Elimination half-life	5.2 hours
Identifiers
	IUPAC name N-(1-Methyl-2-piperidin-1-ylethyl)-N-pyridin-2-ylpropanamide;
CAS Number	15686-91-6 ;
PubChem CID	26216;
ChemSpider	24426 ;
UNII	WT6247U6PX;
CompTox Dashboard (EPA)	DTXSID1023522 ;
ECHA InfoCard	100.036.144
Chemical and physical data
Formula	C16H25N3O
Molar mass	275.396 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N(c1ncccc1)C(CN2CCCCC2)C)CC;
	InChI InChI=1S/C16H25N3O/c1-3-16(20)19(15-9-5-6-10-17-15)14(2)13-18-11-7-4-8-12-18/h5-6,9-10,14H,3-4,7-8,11-13H2,1-2H3 ; Key:ZBAFFZBKCMWUHM-UHFFFAOYSA-N ;
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Propiram (Algeril, Dirame, Bay 4503)^[2] is a partial μ-opioid receptor agonist and weak μ antagonist analgesic from the ampromide family of drugs related to other drugs such as phenampromide and diampromide. It was invented in 1963 in the United Kingdom by Bayer^[3] but was not widely marketed, although it saw some limited clinical use, especially in dentistry. Propiram reached Phase III clinical trials in the United States and Canada.^[4]

^ 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 2023-08-03.
^ US3163654A Pyridine derivatives and their preparation (n-tertiary aminoalkyl-n-acyl)-amino pyridines
^ U.S. patent 3,163,654
^ Drug Facts & Comparisons (56th ed.). 2002.

[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 2023-08-03.

[2] US3163654A Pyridine derivatives and their preparation (n-tertiary aminoalkyl-n-acyl)-amino pyridines

[3] U.S. patent 3,163,654

[4] Drug Facts & Comparisons (56th ed.). 2002.

[1]

[2]

[3]

[4]

Clinical data

Routes of administration	By mouth, injected
ATC code	none
Legal status
Legal status	AU: S8 (Controlled drug) BR: Class A2 (Narcotic drugs)^[1] CA: Schedule I DE: Anlage II (Authorized trade only, not prescriptible) US: Schedule I
Pharmacokinetic data
Bioavailability	97%
Elimination half-life	5.2 hours
Identifiers
IUPAC name N-(1-Methyl-2-piperidin-1-ylethyl)-N-pyridin-2-ylpropanamide
CAS Number	15686-91-6^N
PubChem CID	26216
ChemSpider	24426^Y
UNII	WT6247U6PX
CompTox Dashboard (EPA)	DTXSID1023522
ECHA InfoCard	100.036.144
Chemical and physical data
Formula	C₁₆H₂₅N₃O
Molar mass	275.396 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(N(c1ncccc1)C(CN2CCCCC2)C)CC
InChI InChI=1S/C16H25N3O/c1-3-16(20)19(15-9-5-6-10-17-15)14(2)13-18-11-7-4-8-12-18/h5-6,9-10,14H,3-4,7-8,11-13H2,1-2H3^Y Key:ZBAFFZBKCMWUHM-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)