Solasodine

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Names

[ CAS No. ]:
126-17-0

[ Name ]:
Solasodine

[Synonym ]:
(3b,22a,25R)-Spirosol-5-en-3-ol
Solanearpidine
Solasod-5-en-3β-ol
(3β,22α,25R)-Spirosol-5-en-3-ol
Solancarpidine
Solasod-5-en-3b-ol
Solasod-5-en-3β-ol (8CI)
Purapuridine
MFCD00037844
EINECS 204-774-2
Solasod-5-en-3-β-ol
Solanidine-S
Solasodine
Spirosol-5-en-3-ol, (3β,22α,25R)-
D5-20bF,22aF,25aF,28-azaspirosten-3b-ol

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
537.9±50.0 °C at 760 mmHg

[ Melting Point ]:
284 °C (dec.)(lit.)

[ Molecular Formula ]:
C₂₇H₄₃NO₂

[ Molecular Weight ]:
413.636

[ Flash Point ]:
279.1±30.1 °C

[ Exact Mass ]:
413.329376

[ PSA ]:
41.49000

[ LogP ]:
5.78

[ Vapour Pressure ]:
0.0±3.2 mmHg at 25°C

[ Index of Refraction ]:
1.572

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
200 g/L (25 ºC)

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WF1300000

CHEMICAL NAME :: Solasod-5-en-3-beta-ol

CAS REGISTRY NUMBER :: 126-17-0

BEILSTEIN REFERENCE NO. :: 0094578

LAST UPDATED :: 199612

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C27-H43-N-O2

MOLECULAR WEIGHT :: 413.71

WISWESSER LINE NOTATION :: T F5 E5 B666 HXO OUTJ A1 E1 G1 RQ H-& BT6MXTJ E1

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 :: 4978 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - other (direct) parasympathomimetic Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 396 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - other (direct) parasympathomimetic Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 27500 ug/kg

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

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 24,469,1961

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 899 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - other (direct) parasympathomimetic Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 103 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - other (direct) parasympathomimetic Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 37,719,1974

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 1200 mg/kg

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

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 17,327,1978 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4250 mg/kg/4W-I

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Kidney, Ureter, Bladder - interstitial nephritis Related to Chronic Data - death

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 37,719,1974

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3375 mg/kg/5W-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), zonal Liver - changes in liver weight Blood - changes in leukocyte (WBC) count

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 120 mg/kg/8D-I

TOXIC EFFECTS :: Related to Chronic Data - death

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 24,469,1961 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 120 mg/kg

SEX/DURATION :: female 6-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,1187,1973

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 300 mg/kg

SEX/DURATION :: male 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct

REFERENCE :: IJANDP International Journal of Andrology. (Scriptor Publisher ApS, 15 Gasvaerksvej, DK-1656 Copenhagen V, Denmark) V.1- 1978- Volume(issue)/page/year: 5,295,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 15 gm/kg

SEX/DURATION :: male 150 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: ANDRDQ Andrologia. (Grosse Verlag GmbH, Kurfuerstenstr. 112-113, D-1000 Berlin 30, Fed. Rep. Ger.) V.6- 1974- Volume(issue)/page/year: 21,542,1989

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1500 mg/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: BECTA6 Bulletin of Environmental Contamination and Toxicology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1966- Volume(issue)/page/year: 15,522,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1184 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

REFERENCE :: RCOCB8 Research Communications in Chemical Pathology and Pharmacology. (PJD Pub. Ltd., P.O. Box 966, Westbury, NY 11590) V.1- 1970- Volume(issue)/page/year: 13,723,1976

Safety Information

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
WF1300000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

16,28-Secosolanid-5-ene-3,16-diol, (3beta,16beta,22alpha,25beta)-
Solasonine
Solasodine, hydrochloride
16,22-diketo-26-iodocholesterol
(25R)-3β-hydroxy-26-(toluene-4-sulfonyloxy)-cholest-5-ene-16,22-dione
Cryptogenin
O4-(22R,25R)-spirosol-3-en-3β-yl-β-L-6-deoxy-mannopyranosyl β-D-glucopyranoside
(22S:25R)-N-Chlor-22,26-imino-cholest-5-en-3β,16β-diol

DownStream

16-Dehydropregenolone Acetate
3β-Acetyloxy-16α-methoxypregn-5-en-20-one
Spirosol-4-en-3-one,(22a,25R)- (9CI)

Related Compounds

Acetylsolasodine
N,O-diacetylsolasodine
Solasodine hydrochloride
solasodine α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside
tert-Butyl 2-(6-(diisopropylamino)pyridin-3-yl)pyrrolidine-1-carboxylate
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
(4-Methyl-tetrahydro-furan-2-yl)-methanol
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
[1-(dimethyl-1H-1,2,4-triazol-5-yl)propyl](methyl)amine
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
tert-Butyl-DL-alanine