22881-35-2

Basic information

• Product Name: FAMPROFAZONE
• Synonyms: 4-Isopropyl-2-methyl-3-{[methyl(alpha-methylphenethyl)amino]methyl}-1-phenyl-3-pyrazolin-5-one;4-isopropyl-3-(alpha-(methyl-(1-phenyl-2-propyl)amino))-antipyrin;Antipyrine, 4-isopropyl-3-(alpha-(methyl-(1-phenyl-2-propyl)amino))-;component of Gewodin;ipyrine;o)methyl-;Pyrazolin-5-one, 4-isopropyl-2-methyl-1-phenyl-3-((1-phenyl-2-propyl)methylamino)methyl-;pyrazolin-5-one,4-isopropyl-2-methyl-1-phenyl-3-((1-phenyl-2-propyl)methylamin
• CAS NO: 22881-35-2
• Molecular Formula: C₂₄H₃₁N₃O
• Molecular Weight: 377.52
• EINECS: 245-284-9
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 22881-35-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 132-133 °C(Solv: ethanol (64-17-5))
• Boiling Point: 485.1°Cat760mmHg
• Flash Point: 184.8°C
• Appearance: /
• Density: 1.083g/cm³
• Vapor Pressure: 1.45E-09mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly)
• PKA: 10.28±0.50(Predicted)
• CAS DataBase Reference: FAMPROFAZONE(CAS DataBase Reference)
• NIST Chemistry Reference: FAMPROFAZONE(22881-35-2)
• EPA Substance Registry System: FAMPROFAZONE(22881-35-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: UQ9451000
• Hazardous Substances Data: 22881-35-2(Hazardous Substances Data)

Usage

Description

Famprofazone is a pharmaceutical compound that has been known to metabolize into Methamphetamine (M258795) and Amphetamine (A634248). Due to its potential for abuse and health risks, it is listed as a controlled substance and is prohibited by the World Anti-Doping Agency.

Uses

Used in Pharmaceutical Industry:
Famprofazone is used as an analgesic for its pain-relieving properties, as an antipyretic to reduce fever, and as a CNS stimulant to increase alertness and attention.
Used in Sports and Performance Enhancement:
Famprofazone is used as a prohibited substance in the context of sports and performance enhancement due to its conversion into Methamphetamine and Amphetamine, which can provide unfair advantages in athletic competitions. Its use is strictly regulated and monitored by the World Anti-Doping Agency to ensure fair play and protect the health of athletes.

InChI:InChI=1/C24H31N3O/c1-18(2)23-22(17-25(4)19(3)16-20-12-8-6-9-13-20)26(5)27(24(23)28)21-14-10-7-11-15-21/h6-15,18-19H,16-17H2,1-5H3

Synthetic route

Famprofazon N-oxide (88913-09-1) → allylbenzene (300-57-2) + 1-phenyl-2-dimethylaminopropane (4075-96-1) + Famprofazone (22881-35-2) + 3-(N-Hydroxy-N-methylaminomethyl)-4-isopropyl-2-methyl-1-phenyl-3-pyrazolin-5-on (88913-10-4) + 3-Formyl-4-isopropyl-2-methyl-1-phenyl-3-pyrazolin-5-on (83957-93-1) + 4-Isopropyl-2-methyl-3-(N-methyl-aminomethyl)-1-phenyl-3-pyrazolin-5-on (83957-94-2)

Conditions	Yield
In dichloromethane for 72h; Product distribution; Ambient temperature; various time, various solvent;

Famprofazon N-oxide (88913-09-1) → 1-phenyl-2-dimethylaminopropane (4075-96-1) + Famprofazone (22881-35-2) + 3-Formyl-4-isopropyl-2-methyl-1-phenyl-3-pyrazolin-5-on (83957-93-1) + 4-Isopropyl-2-methyl-3-(N-methyl-aminomethyl)-1-phenyl-3-pyrazolin-5-on (83957-94-2) + 4-Isopropyl-2-methyl-3- (88913-08-0)

Conditions	Yield
With tartaric acid; ferric nitrate In water for 24h; Product distribution; Heating; also with 0.1 N HCl; various time;

Famprofazone (22881-35-2) → methamphetamin (7632-10-2) + 5-(hydroxymethyl)-4-isopropyl-1-methyl-2-phenyl-1H-pyrazol-3(2H)-one (83957-89-5) + 2-Methyl-3- + 3-Formyl-4-isopropyl-2-methyl-1-phenyl-3-pyrazolin-5-on (83957-93-1) + 4-Isopropyl-2-methyl-3-(N-methyl-aminomethyl)-1-phenyl-3-pyrazolin-5-on (83957-94-2) + 4-Isopropyl-2-methyl-3- (88913-08-0)

Conditions	Yield
With hydrogenchloride for 100h; Product distribution; Heating;

Famprofazone (22881-35-2) → 4-Isopropyl-1-methyl-5-{[methyl-(1-methyl-2-phenyl-ethyl)-amino]-methyl}-2-phenyl-1,2-dihydro-pyrazol-3-one; hydrochloride (91485-56-2)

Conditions	Yield
With hydrogenchloride In diethyl ether

Famprofazone (22881-35-2) → Famprofazon N-oxide (88913-09-1)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 5℃; for 0.166667h; Yield given;

Upstream product

• 88913-09-1 Famprofazon N-oxide 

Downstream Products

• 7632-10-2 methamphetamin 
• 83957-89-5 5-(hydroxymethyl)-4-isopropyl-1-methyl-2-phenyl-1H-pyrazol-3(2H)-one 
• 83957-93-1 3-Formyl-4-isopropyl-2-methyl-1-phenyl-3-pyrazolin-5-on 
• 83957-94-2 4-Isopropyl-2-methyl-3-(N-methyl-aminomethyl)-1-phenyl-3-pyrazolin-5-on 
• 88913-08-0 4-Isopropyl-2-methyl-3--1-phenyl-3-pyrazolin-5-on 
• 91485-56-2 4-Isopropyl-1-methyl-5-{[methyl-(1-methyl-2-phenyl-ethyl)-amino]-methyl}-2-phenyl-1,2-dihydro-pyrazol-3-one; hydrochloride 
• 88913-09-1 Famprofazon N-oxide 

Relevant articles and documents

Investigations on the Stability of Famprofazon N-Oxide

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