Jervine

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Names

[ CAS No. ]:
469-59-0

[ Name ]:
Jervine

[Synonym ]:
17,23β-Epoxy-3β-hydroxyveratraman-11-one
(3β, 23β)-17,23-Epoxy-3-hydroxyveratraman-11-one
(3β,22S,23R)-3-Hydroxy-17,23-epoxyveratraman-11-one
Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3-β,23-β)- (9CI)
DL-ISOLEUCINE GRADE II
(3b,23b)-17,23-Epoxy-3-hydroxyveratraman-11-one
4-27-00-03590 (Beilstein Handbook Reference)
(3β,23β)-17,23-Epoxy-3-hydroxyveratraman-11-one
Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3β,23β)-
11-KETOCYCLOPAMINE
Iervin
Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3β,23β)- (9CI)
jerwiny
Jervin-11-one
Spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-11(1H)-one, 2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11a,11b-hexadecahydro-3-hydroxy-3',6',10,11b-tetramethyl-, (3S,3'R,3a'S,6'S,6aS,6bS,7a'R,9R,11aS,11bR)-

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
592.0±50.0 °C at 760 mmHg

[ Melting Point ]:
242- 244ºC

[ Molecular Formula ]:
C₂₇H₃₉NO₃

[ Molecular Weight ]:
425.603

[ Flash Point ]:
311.8±30.1 °C

[ Exact Mass ]:
425.292999

[ PSA ]:
58.56000

[ LogP ]:
3.46

[ Vapour Pressure ]:
0.0±3.8 mmHg at 25°C

[ Index of Refraction ]:
1.591

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WG9700000

CHEMICAL NAME :: Spiro(9H-benzo(a)fluorene-9,2'(3'H)-furo(3,2-b)-pyrid in)-11(1H)-one, 2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11a,11b-hexadec ahydro-3-hydroxy- 3',6',10,11b-tetramethyl-

CAS REGISTRY NUMBER :: 469-59-0

BEILSTEIN REFERENCE NO. :: 0059109

LAST UPDATED :: 199709

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C27-H39-N-O3

MOLECULAR WEIGHT :: 425.67

WISWESSER LINE NOTATION :: L D6 B566 CV 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 - rat

DOSE/DURATION :: 240 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 :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 260 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: 42,105,1990

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15 mg/kg

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

REFERENCE :: DIPHAH Dissertationes Pharmaceuticae. (Warsaw, Poland) V.1-17, 1949-65. For publisher information, see PJPPAA. Volume(issue)/page/year: 8,9,1956

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 29 mg/kg

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

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 113,89,1955

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 80 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 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 400 mg/kg

SEX/DURATION :: female 8-12 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 :: 150 mg/kg

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

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) 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: 42,105,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 66700 ug/kg

SEX/DURATION :: female 7 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: 136,1174,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 55500 ug/kg

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

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous 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: 136,1174,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 127 mg/kg

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

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - eye/ear

REFERENCE :: 41CIAR "Effects of Poisonous Plants on Livestock, Proceedings of a Joint U.S.-Australian Symposium on Poisonous Plants, Logan, UT, 1977," Keeler, R.F., et al. eds., New York, Academic Press, Inc., 1978 Volume(issue)/page/year: -,409,1978

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 - 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 :: 80 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 :: 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 *** REVIEWS *** TOXICOLOGY REVIEW LYPHAD Lyon Pharmaceutique. (Medipharly, 12, rue de la Barre, 69002 Lyons, France) V.1- 1950- Volume(issue)/page/year: 26,5,1975 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

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
WG9700000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Development of an enzyme-linked immunosorbent assay for the veratrum plant teratogens: cyclopamine and jervine.

J. Agric. Food Chem. 51(3) , 582-6, (2003)

Veratrum californicum was responsible for large losses of sheep grazing high mountain ranges in central Idaho in the 1950s. Veratrum induces various birth defects including the cyclopic-type craniofac...

Cyclopamine and jervine induce COX-2 overexpression in human erythroleukemia cells but only cyclopamine has a pro-apoptotic effect.

Exp. Cell Res. 319(7) , 1043-53, (2013)

Erythroleukemia is generally associated with a very poor response and survival to current available therapeutic agents. Cyclooxygenase-2 (COX-2) has been described to play a crucial role in the prolif...

Effects of Veratrum nigrum alkaloids on central catecholaminergic neurons of renal hypertensive rats.

Acta Pharmacol. Sin. 21(1) , 23-8, (2000)

To study the central hypotensive mechanism of Veratrum nigrum L var ussurience Nakai alkaloids (VnA) in renal hypertensive rats(RHR).The quantitative method of immunocytochemistry (ICC) was used to ob...