Product Name

  • Name

    Trihexylphenedyl

  • EINECS 205-614-4
  • CAS No. 144-11-6
  • Density 1.041 g/cm3
  • Solubility
  • Melting Point 258.5 °C
  • Formula C20H31NO
  • Boiling Point 447.852 °C at 760 mmHg
  • Molecular Weight 301.472
  • Flash Point 210.982 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 144-11-6 (Trihexylphenedyl)
  • Hazard Symbols
  • Synonyms Benzhexol;NSC12268;a-Cyclohexyl-a-phenyl-1-piperidinepropanol;Trihexylphenedyl;
  • PSA 23.47000
  • LogP 4.26840

Synthetic route

1-cyclohexyl-3-piperidino-propan-1-one
30257-63-7

1-cyclohexyl-3-piperidino-propan-1-one

phenylmagnesium bromide

phenylmagnesium bromide

trihexyphenidyl
144-11-6

trihexyphenidyl

Conditions
ConditionsYield
With diethyl ether
With benzene
1-phenyl-3-(piperidin-1-yl)propan-1-one
73-63-2

1-phenyl-3-(piperidin-1-yl)propan-1-one

cyclohexylmagnesium bromide
931-50-0

cyclohexylmagnesium bromide

trihexyphenidyl
144-11-6

trihexyphenidyl

Conditions
ConditionsYield
With diethyl ether
Pridinol
511-45-5

Pridinol

trihexyphenidyl
144-11-6

trihexyphenidyl

Conditions
ConditionsYield
With acetic acid; platinum Hydrogenation;
piperidine
110-89-4

piperidine

(+/-)-3-chloro-1-cyclohexyl-1-phenyl-propan-1-ol

(+/-)-3-chloro-1-cyclohexyl-1-phenyl-propan-1-ol

trihexyphenidyl
144-11-6

trihexyphenidyl

1-bromocyclohexane
108-85-0

1-bromocyclohexane

bromobenzene
108-86-1

bromobenzene

ethyl piperidine-1-propionate
19653-33-9

ethyl piperidine-1-propionate

A

trihexyphenidyl
144-11-6

trihexyphenidyl

B

other compounds

other compounds

Conditions
ConditionsYield
With diethyl ether; magnesium; toluene
piperidine
110-89-4

piperidine

trihexyphenidyl
144-11-6

trihexyphenidyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: benzene
View Scheme
3-chloro-1-cyclohexyl-propan-1-one
13487-73-5

3-chloro-1-cyclohexyl-propan-1-one

trihexyphenidyl
144-11-6

trihexyphenidyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: benzene
View Scheme
trihexyphenidyl
144-11-6

trihexyphenidyl

trihexyphenidyl N-oxide

trihexyphenidyl N-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at -70℃; for 0.5h;52%
succinoyl dichloride
543-20-4

succinoyl dichloride

trihexyphenidyl
144-11-6

trihexyphenidyl

trihexyphenidyl hemisuccinate

trihexyphenidyl hemisuccinate

Conditions
ConditionsYield
In chloroform for 1h;45%
trihexyphenidyl
144-11-6

trihexyphenidyl

1-(3ξ-cyclohexyl-3ξ-phenyl-allyl)-piperidine
67562-42-9

1-(3ξ-cyclohexyl-3ξ-phenyl-allyl)-piperidine

Conditions
ConditionsYield
With hydrogenchloride; acetic acid
trihexyphenidyl
144-11-6

trihexyphenidyl

1-(3-cyclohex-1-enyl-3-phenyl-propyl)-piperidine
29869-47-4

1-(3-cyclohex-1-enyl-3-phenyl-propyl)-piperidine

Conditions
ConditionsYield
With phosphorus; hydrogen iodide; acetic acid
trihexyphenidyl
144-11-6

trihexyphenidyl

hydroxytrihexyphenidyl

hydroxytrihexyphenidyl

Conditions
ConditionsYield
With phosphate buffer; potassium chloride; magnesium chloride In methanol; water at 37℃; microsomal homogenate from liver of two female Lewis rats, nicotinamide adenine dinucleotide phosphate, glucose-6-phosphate, glucose-6-phosphate dehydrogenase; pH 7.4;
trihexyphenidyl
144-11-6

trihexyphenidyl

A

(+)-Trihexyphenidyl
40520-24-9

(+)-Trihexyphenidyl

B

(-)-Trihexyphenidyl
40520-25-0

(-)-Trihexyphenidyl

hydrogenchloride
7647-01-0

hydrogenchloride

acetic acid
64-19-7

acetic acid

trihexyphenidyl
144-11-6

trihexyphenidyl

1-<3-cyclohexyl-3-phenyl-allyl>-piperidine hydrochloride

1-<3-cyclohexyl-3-phenyl-allyl>-piperidine hydrochloride

acetic acid
64-19-7

acetic acid

trihexyphenidyl
144-11-6

trihexyphenidyl

aqueous hydrogen iodide

aqueous hydrogen iodide

red phosphorus

red phosphorus

1-(3-cyclohex-1-enyl-3-phenyl-propyl)-piperidine
29869-47-4

1-(3-cyclohex-1-enyl-3-phenyl-propyl)-piperidine

trihexyphenidyl
144-11-6

trihexyphenidyl

1-(3,3-dicyclohexyl-propyl)-piperidine

1-(3,3-dicyclohexyl-propyl)-piperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrochloric acid , concentrated aqueous; acetic acid
2: platinum; ethanol / Hydrogenation
View Scheme
Multi-step reaction with 3 steps
1: hydrochloric acid , concentrated aqueous; acetic acid
2: palladium/charcoal; ethanol / Hydrogenation
3: platinum; ethanol / Hydrogenation
View Scheme
trihexyphenidyl
144-11-6

trihexyphenidyl

1-(3-cyclohexyl-3-phenyl-propyl)-piperidine
29869-50-9

1-(3-cyclohexyl-3-phenyl-propyl)-piperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrochloric acid , concentrated aqueous; acetic acid
2: palladium/charcoal; ethanol / Hydrogenation
View Scheme

Trihexylphenedyl Specification

The Trihexylphenedyl, with the CAS registry number 144-11-6,is also known as Artane; Benzhexol; 1-Cyclohexyl-1-phenyl-3-(1-piperidyl)propan-1-ol. It belongs to the product categories of API.Its EINECS number is 205-614-4. This chemical's molecular formula is C20H31NO and molecular weight is 301.47. What's more,Its systematic name is Trihexylphenedyl.It is one of the centrally acting muscarinic antagonists used for treatment of parkinsonian disorders and drug-induced extrapyramidal movement disorders and as an antispasmodic.It was invented in the United States in 1949, and it has been in clinical usage for decades. Chemically, it is a tertiary amine with alcohol, phenyl, and cyclohexyl moieties. The drug is available as the hydrochloride salt.

Physical properties about Trihexyphenidyl are:
(1)ACD/LogP:  4.391; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  1.37; (4)ACD/LogD (pH 7.4):  2.50; (5)ACD/BCF (pH 5.5):  1.21; (6)ACD/BCF (pH 7.4):  16.34; (7)ACD/KOC (pH 5.5):  5.52; (8)ACD/KOC (pH 7.4):  74.45; (9)#H bond acceptors:  2; (10)#H bond donors:  1; (11)#Freely Rotating Bonds:  6; (12)Index of Refraction:  1.547; (13)Molar Refractivity:  91.847 cm3; (14)Molar Volume:  289.671 cm3; (15)Surface Tension:  43.3380012512207 dyne/cm; (16)Density:  1.041 g/cm3; (17)Flash Point:  210.982 °C; (18)Enthalpy of Vaporization:  74.43 kJ/mol; (19)Boiling Point:  447.852 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:OC(c1ccccc1)(CCN2CCCCC2)C3CCCCC3;
(2)Std. InChI:InChI=1S/C20H31NO/c22-20(18-10-4-1-5-11-18,19-12-6-2-7-13-19)14-17-21-15-8-3-9-16-21/h1,4-5,10-11,19,22H,2-3,6-9,12-17H2;
(3)Std. InChIKey:HWHLPVGTWGOCJO-UHFFFAOYSA-N.

Uses of Trihexyphenidyl:
Trihexyphenidyl is used for the symptomatic treatment of Parkinson's disease in mono- and combination therapy. It is active in postencephalitic, arteriosclerotic, and idiopathic forms. The drug is also commonly used to treat extrapyramidal side effects occurring during antipsychotic treatment. It reduces the frequency and duration of oculogyric crises as well as of dyskinetic movements and spastic contractions. Excessive salivation may also respond. Trihexyphenidyl may improve psychotic depression and mental inertia frequently associated with Parkinson's disease and symptomatic problems caused by antipsychotic treatment.
According to a recent news report, trihexyphenidyl has been used recreationally among Iraqi soldiers and police. The report states that the drug, taken in high doses, results in an increased sense of well-being and decreased anxiety. Although the drug is not considered physically addictive, the report suggests that the drug may become habit forming among some users due to its supposed psychological effects.

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