Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)-

Modify Date: 2024-01-10 14:44:01

Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)- Structure
Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)- structure
Common Name Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)-
CAS Number 2731-16-0 Molecular Weight 373.46600
Density 1.27g/cm3 Boiling Point 631.6ºC at 760mmHg
Molecular Formula C20H23NO4S Melting Point N/A
MSDS N/A Flash Point 335.8ºC

 Names

Name (7S)-7-amino-1,2,3-trimethoxy-10-methylsulfanyl-6,7-dihydro-5H-benzo[a]heptalen-9-one
Synonym More Synonyms

 Chemical & Physical Properties

Density 1.27g/cm3
Boiling Point 631.6ºC at 760mmHg
Molecular Formula C20H23NO4S
Molecular Weight 373.46600
Flash Point 335.8ºC
Exact Mass 373.13500
PSA 96.08000
LogP 4.10780
Vapour Pressure 7.33E-16mmHg at 25°C
Index of Refraction 1.624

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GH0875000
CHEMICAL NAME :
Colchicine, N-deacetyl-10-thio-
CAS REGISTRY NUMBER :
2731-16-0
BEILSTEIN REFERENCE NO. :
2822164
LAST UPDATED :
199612
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C20-H23-N-O4-S
MOLECULAR WEIGHT :
373.50
WISWESSER LINE NOTATION :
L B677 MV&T&J CO1 DO1 EO1 JZ NS1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human
DOSE/DURATION :
71 ug/kg/D
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting Blood - leukopenia
REFERENCE :
BAFEAG Bulletin de l'Association Francaise pour l'Etude du Cancer. (Paris, France) V.1-52, 1908-65. For publisher information, see BUCABS. Volume(issue)/page/year: 42,308,1955
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
175 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: 98,479,1958
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
37 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: 98,479,1958
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intracerebral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 109,386,1957
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2000 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 15,533,1960
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BAFEAG Bulletin de l'Association Francaise pour l'Etude du Cancer. (Paris, France) V.1-52, 1908-65. For publisher information, see BUCABS. Volume(issue)/page/year: 42,308,1955
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
66 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 24,636,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 107,150,1956 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
6 mg/kg
SEX/DURATION :
female 13-14 week(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
ACEDAB Acta Endocrinologica, Supplementum (Copenhagen). (Periodica, Skolegade 12 E, DK-2500 Valby, Denmark) No.1- 1948- Volume(issue)/page/year: 166,435,1972

 Safety Information

HS Code 2930909090

 Synthetic Route

~66%

Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)- Structure

Benzo[a]heptale...

CAS#:2731-16-0

Literature: Lee, Sun-Hee; Park, Sun-Kyoung; Kim, Jeong-Mi; Kim, Myung-Hwa; Kim, Kwang-Hee; Chun, Kwang-Woo; Cho, Kyung-Hea; Youn, Ji-Youn; Namgoong, Sung Keon Archiv der Pharmazie, 2005 , vol. 338, # 12 p. 582 - 589

~%

Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)- Structure

Benzo[a]heptale...

CAS#:2731-16-0

Literature: Chang, Dong-Jo; Kim, Wan-Joo Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 14 p. 3121 - 3125

~10%

Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)- Structure

Benzo[a]heptale...

CAS#:2731-16-0

Literature: Shi, Qian; Verdier-Pinard, Pascal; Brossi, Arnold; Hamel, Ernest; Lee, Kuo-Hsiung Bioorganic and Medicinal Chemistry, 1997 , vol. 5, # 12 p. 2277 - 2282

~%

Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)- Structure

Benzo[a]heptale...

CAS#:2731-16-0

Literature: Shi, Qian; Verdier-Pinard, Pascal; Brossi, Arnold; Hamel, Ernest; Lee, Kuo-Hsiung Bioorganic and Medicinal Chemistry, 1997 , vol. 5, # 12 p. 2277 - 2282

~%

Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)- Structure

Benzo[a]heptale...

CAS#:2731-16-0

Literature: Shi, Qian; Verdier-Pinard, Pascal; Brossi, Arnold; Hamel, Ernest; Lee, Kuo-Hsiung Bioorganic and Medicinal Chemistry, 1997 , vol. 5, # 12 p. 2277 - 2282
Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)- Structure

Benzo[a]heptale...

CAS#:2731-16-0

~%

Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)- Structure

Benzo[a]heptale...

CAS#:2731-16-0

Literature: Shi, Qian; Verdier-Pinard, Pascal; Brossi, Arnold; Hamel, Ernest; Lee, Kuo-Hsiung Bioorganic and Medicinal Chemistry, 1997 , vol. 5, # 12 p. 2277 - 2282

 Customs

HS Code 2930909090
Summary 2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

 Synonyms

N-Deacetylmethylthiocolchicine
Desacetyl thiocolchicine
(S)-7-amino-1,2,3-trimethoxy-10-methylsulfanyl-6,7-dihydro-5H-benzo[a]heptalen-9-one
deacetyl-10-thiocolchicine
N-deacetyl thiocolchicine
Colchicine,N-deacetyl-thio
Thiolcolciran
7-deacetylthiocolchicine
Corps R. 261
N-Desacetylthiocolchicine
Thio-colciran
Deacetylthiocolchicine