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Basic Information
CAS No.: 437-38-7
Name: Propanamide,N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-
Article Data: 26
Cas Database
Molecular Structure:
Molecular Structure of 437-38-7 (Propanamide,N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-)
Formula: C22H28N2O
Molecular Weight: 336.477
Synonyms: Propionanilide,N-(1-phenethyl-4-piperidyl)- (7CI,8CI);1-Phenethyl-4-(N-phenylpropionamido)piperidine;1-Phenethyl-4-N-propionylanilinopiperidine;Durogesic D-Trans;Durotep MT;Fentanest;Fentanil;Fentanyl;Fentora;Matrifen;N-(1-Phenethylpiperidin-4-yl)-N-phenylpropionamide;N-[1-(2-Phenylethyl)-4-piperidinyl]propionanilide;
EINECS: 207-113-6
Density: 1.087 g/cm3
Melting Point: 83-84 °C
Boiling Point: 466.2 °C at 760 mmHg
Flash Point: 185.8 °C
Solubility: 0.2g/L(25 oC)
Appearance: Pale brown solid
Hazard Symbols: F,T
Risk Codes: 11-23/25-36/38-39/23/24/25-23/24/25
Safety: 16-24-45-36/37-7
Transport Information: N/A
PSA: 23.55000
LogP: 4.07460
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Fentanyl (437-38-7) was first synthesized by Paul Janssen under the label of his relatively newly formed Janssen Pharmaceutica in 1959. In the 1960s, fentanyl was introduced as an intravenous anesthetic under the trade name of Sublimaze. In the mid-1990s, Janssen Pharmaceutica developed and introduced into clinical trials the Duragesic patch..
Following the patch, a flavored lollipop of fentanyl citrate mixed with inert fillers was introduced under the brand name of Actiq, becoming the first quick-acting formation of fentanyl for use with chronic breakthrough pain. More recently, fentanyl has been developed into an effervescent tab for buccal absorption much like the Actiq lollipop, followed by a buccal spray device for fast-acting relief and other delivery methods currently in development.
A new Fentanyl product has just been approved by the FDA for breakthrough cancer pain called Onsolis. There appears to be less abuse potential because the drug can not be crushed up and snorted like other Fentanyl product. It also has less of a chance of causing mouth ulcers for patients needing to use Fentanyl for breakthrough cancer pain.


The Phentanyl with CAS registry number of 437-38-7 is also known as Propanamide,N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-. The IUPAC name is N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide. It belongs to product categories of Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 207-113-6. In addition, the formula is C22H28N2O and the molecular weight is 336.47. What's more, it can be used as an analgesic and controlled substance.

Physical properties about Phentanyl are: (1)ACD/LogP: 3.89; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.02; (4)ACD/LogD (pH 7.4): 2.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 23.4; (7)ACD/KOC (pH 5.5): 4.24; (8)ACD/KOC (pH 7.4): 136.78; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.584; (13)Molar Refractivity: 103.66 cm3; (14)Molar Volume: 309.3 cm3; (15)Surface Tension: 45.7 dyne/cm; (16)Density: 1.087 g/cm3; (17)Flash Point: 185.8 °C; (18)Enthalpy of Vaporization: 72.79 kJ/mol; (19)Boiling Point: 466.2 °C at 760 mmHg; (20)Vapour Pressure: 7.25E-09 mmHg at 25 °C.

Uses of Phentanyl: it is used to produce N-[1-(2-phenylethyl)-4-piperidinyl]thiopropionanilide. The reaction occurs with reagents P4S10, pyridine, water with other condition of heating for 2 hours. The yield is about 35%.

Phentanyl is used to produce N-[1-(2-phenylethyl)-4-piperidinyl]thiopropionanilide.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
2. InChI: InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo intravenous 2ug/kg (0.002mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

British Medical Journal. Vol. 1, Pg. 278, 1978.
mouse LD50 intraperitoneal 76mg/kg (76mg/kg) BEHAVIORAL: EUPHORIA Pharmaceutical Chemistry Journal Vol. 10, Pg. 1193, 1976.
mouse LD50 intravenous 2900ug/kg (2.9mg/kg)   Toksikologicheskii Vestnik. Vol. (4), Pg. 20, 1995.
mouse LD50 oral 368mg/kg (368mg/kg)   Toksikologicheskii Vestnik. Vol. (4), Pg. 20, 1995.
mouse LD50 subcutaneous 62mg/kg (62mg/kg)   Toksikologicheskii Vestnik. Vol. (4), Pg. 20, 1995.
rat LD intraspinal > 10mg/kg (10mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 56, Pg. 50, 1985.
rat LD50 intravenous 2910ug/kg (2.91mg/kg)   Journal of Medicinal Chemistry. Vol. 17, Pg. 1047, 1974.
rat LD50 oral 18mg/kg (18mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 25, Pg. 929, 1973.
rat LD50 subcutaneous 1500ug/kg (1.5mg/kg)   Pharmaceutical Chemistry Journal Vol. 23, Pg. 395, 1989.
women TDLo oral 100ug/kg (0.1mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

Annals of Emergency Medicine. Vol. 35, Pg. 314, 2000.