Cyclopamine

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Names

[ Name ]:
Cyclopamine

[Synonym ]:
11-DEOXYJERVINE
alkaloidv
Spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol, 1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetramethyl-, (3S,3'R,3a'S,6'S,6aS,6bS,7a'R,9R,11aS,11bR)-
deoxojervine
11-Desoxo-jervin
Veratraman-3-ol, 17,23-epoxy-, (3β,23β)-
Cyclopamine
(3β,22S,23R)-17,23-Epoxyveratraman-3-ol
Spiro(9H-benzo(a)fluorene-9,2'(3'H)-furo(3,2-b)pyridin)-3-ol, 1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetramethyl-, (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-
11-deoxojervine
MFCD01735266
(3β,17β,22S,23R)-17,23-Epoxyveratraman-3-ol
11-deoxo-jervin

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
550.8±50.0 °C at 760 mmHg

[ Melting Point ]:
236-238ºC

[ Molecular Formula ]:
C₂₇H₄₁NO₂

[ Molecular Weight ]:
411.620

[ Flash Point ]:
286.9±30.1 °C

[ Exact Mass ]:
411.313721

[ PSA ]:
41.49000

[ LogP ]:
5.44

[ Vapour Pressure ]:
0.0±3.4 mmHg at 25°C

[ Index of Refraction ]:
1.583

[ Storage condition ]:
2-8°C

[ Stability ]:
Store in Freezer at - 20°C

[ Water Solubility ]:
DMSO: soluble

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GY0750000

CHEMICAL NAME :: Cyclopamine

CAS REGISTRY NUMBER :: 4449-51-8

LAST UPDATED :: 199712

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C27-H41-N-O2

MOLECULAR WEIGHT :: 411.69

WISWESSER LINE NOTATION :: L D6 B566 FX DU LUTJ A1 E1 OQ F-& CT56 BOX FMTJ D1 H1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 180 mg/kg

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

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 170 mg/kg

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

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975 ** 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 - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

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 :: Unreported

DOSE :: 300 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

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: 29(2),22A,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 44500 ug/kg

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

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 136,1174,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 116 mg/kg

SEX/DURATION :: female 7-8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - eye/ear

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 136,1174,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 250 mg/kg

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

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

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 170 mg/kg

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

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 54546 ug/kg

SEX/DURATION :: female 30-31 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 142,1287,1973

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 30 mg/kg

SEX/DURATION :: female 14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 192,153,1989 *** REVIEWS *** TOXICOLOGY REVIEW AEMBAP Advances in Experimental Medicine and Biology. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.1- 1967- Volume(issue)/page/year: 27,107,1972

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Safety Phrases ]:
22-24/25

[ WGK Germany ]:
3

[ RTECS ]:
GY0750000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

(2'R,3S,3'R,3a'S,6aS,6bS,6'S,7a'R,11aS,11bR)-3',6',10,11b-tetramethyl-4'-(phenylsulfonyl)-1,2,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-3-ol
Jervine

DownStream

Related Compounds

Cyclopamine-KAAD
Bodipy Cyclopamine
Despiro Cyclopamine
Cyclopamine tartrate
N-aminoethylcyclopamine
4-(2-(4-Fluoro-3-methylphenyl)pyridin-3-yl)pyridine-2-carbonitrile
Methyl 5-((2,4-difluorobenzyl)carbamoyl)-3-methoxy-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate
2-Cyclopropoxy-4-methylpyridine
2-(tert-butyl) 6-methyl 8-methoxy-3,4-dihydroisoquinoline-2,6(1H)-dicarboxylate
Tert-butyl 8-fluoro-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
8-Fluoro-1,2,3,4-tetrahydroisoquinolin-6-ol
2-(tert-butyl) 6-methyl 8-fluoro-3,4-dihydroisoquinoline-2,6(1H)-dicarboxylate
(2R,5R)-Benzyl 5-formyl-2-methylpiperidine-1-carboxylate
Tert-butyl 8-fluoro-6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1h)-carboxylate
Tert-butyl 5-fluoro-6-hydroxy-8-methyl-3,4-dihydroisoquinoline-2(1h)-carboxylate

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