ChemicalBook CAS DataBase List 21409-26-7

21409-26-7

Name	4-AMINOPHENYL-1-PHENETHYLPIPERIDINE
CAS	21409-26-7
Molecular Formula	C19H24N2
MDL Number	MFCD00179023
Molecular Weight	280.407
MOL File	21409-26-7.mol

Synonyms

4-ANPP TBC-5487 Depropionylfentanyl Fentanyl Related CoMpound E CII N-(1-phenyl-piperidin-4-yl)-aniline 1-Phenethyl-N-phenylpiperidin-4-aMine N-(1-PHENETHYL-PIPERIDIN-4-YL)-ANILINE (1-PHENETHYL-PIPERIDIN-4-YL)-PHENYL-AMINE N-Phenyl-1-(2-phenethyl)piperidin-4-amine N-[1-(2-Phenylethyl)-4-piperidinyl]aniline N-Phenyl-1-(2-phenylethyl)-4-piperidinamine N-PHENYL-1-(2-PHENYLETHYL) PIPERIDIN-4-AMINE 4-Piperidinamine, N-phenyl-1-(2-phenylethyl)- N-[1-(2-Phenylethyl)-4-piperidinyl]benzenamine 4-AMinophenyl-1-phenethylpiperidine (Fentanyl IMpurity) N-Phenyl-N’-[1-(2-phenylethyl)]-4-piperidine Discontinued See: A625875 Fentanyl Related Compound E CII (10 mg) (N-Phenyl-1-(2-phenylethyl)-4-piperidinamine)

Chemical Properties

Appearance	Pale Yellow Solid
Melting point	94-96°C
Boiling point	172-176 °C(Press: 0.15 Torr)
density	1.075±0.06 g/cm3(Predicted)
Fp	9°C
storage temp.	Hygroscopic, -20°C Freezer, Under Inert Atmosphere
solubility	Acetonitrile: Soluble DMSO: Soluble Methanol: Soluble
form	Off-white solid.
pka	9.03±0.10(Predicted)
Major Application	pharmaceutical
InChI	1S/C19H24N2/c1-3-7-17(8-4-1)11-14-21-15-12-19(13-16-21)20-18-9-5-2-6-10-18/h1-10,19-20H,11-16H2
InChIKey	ZCMDXDQUYIWEKB-UHFFFAOYSA-N
SMILES	N2(CCC(CC2)Nc3ccccc3)CCc1ccccc1

Safety Data

Symbol(GHS)	GHS06
Signal word	Danger
Hazard statements	H300+H310+H330
Precautionary statements	P260-P262-P280-P301+P330+P331+P310-P302+P352+P310-P304+P340+P310
Risk Statements	22-36/37/38 less more
Safety Statements	22-37/39-46 less more
RIDADR	UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany	2
HS Code	29333990
Storage Class	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 1 Dermal Acute Tox. 1 Inhalation Acute Tox. 1 Oral
DEA Controlled Substances	CSCN: 8333 CSA SCH: Schedule II NARC: No

Hazard Information

Chemical Properties

Pale Yellow Solid

Uses

A 3H-Fentanyl (F274990) metabolite

Description

4-ANPP (CRM) (Item No. 22700) is a certified reference material that is categorized as a piperidinamine. It is an intermediate in the synthesis of fentanyl (Item Nos. 22659 | 14719 | ISO60197) from N-phenethyl-4-piperidone (NPP; ). As such, 4-ANPP has been used as a precursor for the manufacture of fentanyl and related opioids. 4-ANPP is also an impurity found in fentanyl preparations. It is a known metabolite of acetyl fentanyl (Item Nos. ISO00128 | ISO60128), butyryl fentanyl (Item Nos. 14728 | 19734), furanyl fentanyl (Item Nos. 18705 | 19633), acrylfentanyl , and fentanyl. 4-ANPP is regulated as a Schedule II compound in the United States. This product is intended for research and forensic applications.

Description

4-ANPP (Item No. 18810) is an analytical reference material categorized as an opioid metabolite and a precursor in the synthesis of fentanyl (Item Nos. ISO60197 | 22659 | 14719) and other opioids. 4-ANPP is a metabolite of acetyl fentanyl (Item Nos. ISO60128 | ISO00128), butyryl fentanyl (Item Nos. 19734 | 14728), furanyl fentanyl (Item Nos. 19633 | 18705), acrylfentanyl (Item Nos. 23060 | 19312), and fentanyl. It has also been found as an impurity in illicit fentanyl preparations. 4-ANPP is regulated as a Schedule II compound in the United States. This product is intended for research and forensic applications.

References

[1] R B LABROO. Fentanyl metabolism by human hepatic and intestinal cytochrome P450 3A4: implications for interindividual variability in disposition, efficacy, and drug interactions.[J]. Drug Metabolism and Disposition, 1997, 25 9: 1072-1080.
[2] A. B. MELENT’EV O. N D S S Kataev. Identification and analytical properties of acetyl fentanyl metabolites[J]. Journal of Analytical Chemistry, 2015, 70 2: 240-248. DOI: 10.1134/s1061934815020124
[3] ANDREA E. STEUER. Studies on the metabolism of the fentanyl-derived designer drug butyrfentanyl in human in vitro liver preparations and authentic human samples using liquid chromatography-high resolution mass spectrometry (LC-HRMS)[J]. Drug Testing and Analysis, 2016, 9 7: 1085-1092. DOI: 10.1002/dta.2111
[4] MüLLER M, WUBBOLTS M. Biotransformation Methods for Preparing Chiral Drugs and Drug Intermediates[C]. 2006: 0. DOI: 10.1002/9783527609437.ch4
[5] IRA S. LURIE . Profiling of illicit fentanyl using UHPLC–MS/MS[J]. Forensic science international, 2012, 220 1: Pages 191-196. DOI: 10.1016/j.forsciint.2012.02.024

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