vasicine

Names

[ Name ]:
vasicine

[Synonym ]:
Pyrrolo[2,1-b]quinazolin-3-ol, 1,2,3,9-tetrahydro-, (3R)-
Pyrrolo(2,1-b)quinazolin-3-ol, 1,2,3,9-tetrahydro-
(R)-1,2,3,9-Tetrahydropyrrolo(2,1-b)quinazolin-3-ol
1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol
peganine
(3R)-1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol
Pyrrolo[2,1-b]quinazolin-3-ol, 1,2,3,9-tetrahydro-
vasicin

Biological Activity

[Description]:

Vasicine (peganine) is a quinazoline alkaloid isolated from Justicia adhatoda. Vasicine (peganine) possesses anti- tuberculosis activity[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

[References]

[1]. Grange JM, et al. Activity of bromhexine and ambroxol, semi-synthetic derivatives of vasicine from the Indian shrub Adhatoda vasica, against Mycobacterium tuberculosis in vitro. J Ethnopharmacol. 1996 Jan;50(1):49-53.

Chemical & Physical Properties

[ Density]:
1.1124

[ Boiling Point ]:
373.8±52.0 °C at 760 mmHg

[ Melting Point ]:
211.5°C

[ Molecular Formula ]:
C₁₁H₁₂N₂O

[ Molecular Weight ]:
188.226

[ Flash Point ]:
179.9±30.7 °C

[ Exact Mass ]:
188.094955

[ PSA ]:
35.83000

[ LogP ]:
-1.00

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.5850

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY9454000

CHEMICAL NAME :: Pyrrolo(2,1-b)quinazolin-3-ol, 1,2,3,9-tetrahydro-

CAS REGISTRY NUMBER :: 6159-55-3

LAST UPDATED :: 199510

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C11-H10-N2-O

MOLECULAR WEIGHT :: 186.23

WISWESSER LINE NOTATION :: T C566 BN DV GN HHT&&J

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 79 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IJMRAQ Indian Journal of Medical Research. (Indian Council of Medical Research, Ansari Nagar, New Delhi 110 029, India) V.1- 1913- Volume(issue)/page/year: 66,680,1977

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 79 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PHTXA6 Pharmacology and Toxicology. English translation of FATOAO. (New York, NY) V.20-22, 1957-59. Discontinued. Volume(issue)/page/year: 22,67,1959

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Gastrointestinal - nausea or vomiting Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: PHTXA6 Pharmacology and Toxicology. English translation of FATOAO. (New York, NY) V.20-22, 1957-59. Discontinued. Volume(issue)/page/year: 22,67,1959

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 75 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: PHTXA6 Pharmacology and Toxicology. English translation of FATOAO. (New York, NY) V.20-22, 1957-59. Discontinued. Volume(issue)/page/year: 22,67,1959 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 150 mg/kg

SEX/DURATION :: female 56-60 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 16,1075,1978

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
UN 1544

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933990090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Potentiation of oxytocin evoked responses by (+) sotalol deoxysotalol and Vasicine HCl on isolated rat and rabbit uterus.

Indian J. Med. Res. 76 Suppl , 107-14, (1982)

Natural products as templates for bioactive compound libraries: part 2. Novel modifications of vasicine (peganine) core via efficient and regioselective generation of 3-lithiodeoxyvasicine and its stereoselective addition to aliphatic ketones section sign.

Nat. Prod. Res. 20(9) , 871-81, (2006)

A general procedure for direct lithiation of deoxyvasicine was developed. 3-Lithiodeoxyvasicine intermediate was found to react with various aliphatic ketones providing derivatives of 3-(hydroxyalkyl)...

Formulation and pharmacokinetic evaluation of hard gelatin capsule encapsulating lyophilized Vasa Swaras for improved stability and oral bioavailability of vasicine.

Fitoterapia 82(3) , 446-53, (2011)

The oral bioavailability of vasicine (1) was investigated in hard gelatin capsules of lyophilized Vasa Swaras (aqueous extract of Adhatoda vasica Nees.,Fam.: Acanthaceae) The rat pharmacokinetic profi...