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Vasicine
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Name

Vasicine

 EINECS 228-180-8
CAS No. 6159-55-3 Density 1.37 g/cm3
PSA 35.83000 LogP 0.67030
Solubility N/A Melting Point 182 ºC
Formula C11H12 N2 O Boiling Point 373.8 °C at 760 mmHg
Molecular Weight 188.229 Flash Point 179.9 °C
Transport Information N/A Appearance N/A
Safety Poison by ingestion, intraperitoneal, and subcutaneous routes. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx. Risk Codes 22
Molecular Structure Molecular Structure of 6159-55-3 (VASICINE) Hazard Symbols Xn
Synonyms

Pyrrolo[2,1-b]quinazolin-3-ol,1,2,3,9-tetrahydro-, (S)-;Vasicine (6CI,7CI,8CI);(-)-Linarine;(-)-Peganine;(-)-Vasicine;Linarine, (-)-;Peganin;Peganine;Peganine, (-)-;l-Peganine;l-Vasicine;

Article Data 2

Vasicine Synthetic route

6159-56-4, 176200-11-6

vasicine

6159-55-3

(+)-vasicinol

Conditions
ConditionsYield
With D-tartaric acid
6159-56-4, 176200-11-6

vasicine

A

18549-38-7

vasicine

B

6159-55-3

(+)-vasicinol

Conditions
ConditionsYield
With 2,2'-iminobis[ethanol] In ethanol Resolution of racemate;
6159-55-3

(+)-vasicinol

1227263-77-5

(3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; water for 2h; Solvent;99%
With sodium tetrahydroborate In methanol; water at 20℃; for 2h;99%
With sodium tetrahydroborate; water In methanol at 20℃;90%
6159-55-3

(+)-vasicinol

(3S)-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazolin-3-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 1h; Solvent;95%
6159-55-3

(+)-vasicinol

A

1227263-77-5

(3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol

B

(3S)-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazolin-3-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; water for 2h; Solvent;A 80%
B 10%
39637-99-5, 20445-33-4

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

6159-55-3

(+)-vasicinol

vasicine (R)-α-methoxy-α-(trifluoromethyl)phenylacetic acid ester

20445-33-4, 39637-99-5

(R)-methoxytrifluoromethylphenylacetyl chloride

6159-55-3

(+)-vasicinol

vasicine (S)-α-methoxy-α-(trifluoromethyl)phenylacetic acid ester

6159-55-3

(+)-vasicinol

101385-90-4, 101930-07-8, 101979-03-7, 775-15-5

(R)-N-benzyl-3-hydroxypyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: water; sodium tetrahydroborate / methanol / 10 h / 20 °C
2.1: hypophosphorous acid; sodium azide; sulfuric acid; acetic acid / water / 39.5 h / 5 °C
2.2: pH 8
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
4.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate / methanol; water / 2 h
2.1: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
4.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran / 2 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate / methanol; water / 2 h
2.1: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
4.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran / 2 h / 0 °C
View Scheme
6159-55-3

(+)-vasicinol

101385-90-4

(S)-N-benzyl-3-hydroxypyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water; sodium tetrahydroborate / methanol / 10 h / 20 °C
2.1: hypophosphorous acid; sodium azide; sulfuric acid; acetic acid / water / 39.5 h / 5 °C
2.2: pH 8
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; water / 2 h
2: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; water / 2 h
2: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
View Scheme
6159-55-3

(+)-vasicinol

116143-02-3

(3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water; sodium tetrahydroborate / methanol / 10 h / 20 °C
2.1: hypophosphorous acid; sodium azide; sulfuric acid; acetic acid / water / 39.5 h / 5 °C
2.2: pH 8
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate / methanol; water / 2 h
2.1: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate / methanol; water / 2 h
2.1: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
View Scheme

Vasicine Specification

Vasicine, with the CAS NO.6159-55-3, is also called 1-b)quinazolin-3-ol,1,2,3,9-tetrahydro-pyrrolo(; vasicin; 1,2,3,9-TETRAHYDROPYRROLO[2,1-B]QUINAZOLIN-3-OL; AKOS NCG1-0080; VITAS-BB TBB000541; VASICINE; PEGANINE; C10733. It belongs to the Product Categories of Miscellaneous Natural Products. It is a white to yellow powder and is found in the leaves of the Malabar nut and seeds of the harmal and is thought to poison lower plants and animals but not higher animals.

Physical properties about Vasicine are: (1)ACD/LogP: -0.206; (2)ACD/LogD (pH 5.5): -2.19; (3)ACD/LogD (pH 7.4): -1.72; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.709; (12)Molar Refractivity: 53.452 cm3; (13)Molar Volume: 136.881 cm3; (14)Polarizability: 21.19 10-24cm3; (15)Surface Tension: 55.8619995117188 dyne/cm; (16)Density: 1.375 g/cm3; (17)Flash Point: 179.891 °C; (18)Enthalpy of Vaporization: 65.528 kJ/mol; (19)Boiling Point: 373.837 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2/t10-/m0/s1;
(2)InChIKey=YIICVSCAKJMMDJ-JTQLQIEISA-N;
(3)SmilesN1=C2N(Cc3ccccc13)CC[C@@H]2O

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo subcutaneous 100mg/kg (100mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: EXCITEMENT		 Pharmacology and Toxicology. English translation of FATOAO. Vol. 22, Pg. 67, 1959.
mouse LD50 intraperitoneal 79mg/kg (79mg/kg)   Indian Journal of Medical Research. Vol. 66, Pg. 680, 1977.
mouse LD50 intravenous 79mg/kg (79mg/kg)   Pharmacology and Toxicology. English translation of FATOAO. Vol. 22, Pg. 67, 1959.
rabbit LDLo intravenous 75mg/kg (75mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Pharmacology and Toxicology. English translation of FATOAO. Vol. 22, Pg. 67, 1959.

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