Pentoxyverine

Names

[ CAS No. ]:
77-23-6

[ Name ]:
Pentoxyverine

[Synonym ]:
carbetapentane
Cyclopentanecarboxylic acid, 1-phenyl-, 2-[2-(diethylamino)ethoxy]ethyl ester
2-{[2-(diethylamino)ethyl]oxy}ethyl 1-phenylcyclopentanecarboxylate
Atussil
EINECS 201-014-1
2-[2-(Diethylamino)ethoxy]ethyl 1-phenylcyclopentanecarboxylate
Tuclase
Pentoxyverine
Sedotussin
carbita Pentane
ucb2543
Pentoxyverin
Urex
Pentoxiverin
Pentoxiverine

Biological Activity

[Description]:

Pentoxyverine (Carbetapentane) is a sigma-1 receptor agonist, with a Ki of 75 nM on guinea-pig brain membranes. Pentoxyverine is a centrally-acting cough suppressant with antimuscarinic and anticonvulsant properties. Pentoxyverine can be used for inhibiting bronchial interceptor, weakening of cough reflex, bronchial smooth muscle relaxation and reduction of airway resistance[1][2][3][4].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> Sigma Receptor

[Target]

Ki: 75 nM (sigma-1 receptor)[4]

[In Vitro]

Pentoxyverine competitive binds to [3H]-pentazocine-labelled sites on guinea-pig brain membranes, with a Ki of 75 nM[4].

[In Vivo]

Pentoxyverine (1-5 mg/kg; a single i.p.) inhibits citric-acid-induced cough in guinea-pigs[4].

[References]

[1]. Mohamed SH, et, al. Extraction-free spectrophotometric assay of the antitussive drug pentoxyverine citrate using sulfonephthalein dyes. Spectrochim Acta A Mol Biomol Spectrosc. 2019 Nov 5;222:117186.

[2]. Tortella FC, et, al. Dextromethorphan and carbetapentane: centrally acting non-opioid antitussive agents with novel anticonvulsant properties. Brain Res. 1986 Sep 24;383(1-2):314-8.

[3]. Calderon SN, et, al. Novel 1-phenylcycloalkanecarboxylic acid derivatives are potent and selective sigma 1 ligands. J Med Chem. 1994 Jul 22;37(15):2285-91.

[4]. Brown C, et, al. Antitussive activity of sigma-1 receptor agonists in the guinea-pig. Br J Pharmacol. 2004 Jan;141(2):233-40.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
435.5±30.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₀H₃₁NO₃

[ Molecular Weight ]:
333.465

[ Flash Point ]:
217.2±24.6 °C

[ Exact Mass ]:
333.230408

[ PSA ]:
38.77000

[ LogP ]:
3.29

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.517

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GY3450000

CHEMICAL NAME :: Cyclopentanecarboxylic acid, 1-phenyl-, 2-(2-(diethylamino)ethoxy)ethyl ester

CAS REGISTRY NUMBER :: 77-23-6

BEILSTEIN REFERENCE NO. :: 2299701

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C20-H31-N-O3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 9,446,1957

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 130 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 9,446,1957

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 13 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 9,446,1957

Safety Information

[ Safety Phrases ]:
S26-S36

[ WGK Germany ]:
3

[ HS Code ]:
2921300090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2921300090

[ Summary ]:
2921300090 other cyclanic, cyclenic or cyclotherpenic mono- or polyamines, and their derivatives; salts thereof。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%