Description References
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MONOCROTALINE

Description References
Product Name
MONOCROTALINE
CAS No.
315-22-0
Chemical Name
MONOCROTALINE
Synonyms
CROTALINE;MONOCROTALIN;A 6080;CROTALIN;NSC 28693;NCI-C56462;Bulbus Lilii;MONOCROTALINE;Monccrotalire;MONOCRATALINE
CBNumber
CB4361934
Molecular Formula
C16H23NO6
Formula Weight
325.36
MOL File
315-22-0.mol
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MONOCROTALINE Property

Melting point:
204 °C (dec.) (lit.)
alpha 
-54.8o (C=5 IN CHLOROFORM)
Boiling point:
463.55°C (rough estimate)
Density 
1.1512 (rough estimate)
refractive index 
1.5500 (estimate)
storage temp. 
2-8°C
solubility 
Soluble in DMSO (up to 50 mg/ml with warming), in Ethanol (up to 10 mg/ml with warming) or in organic solvents such as Chloroform (up to 50 mg/ml)
form 
Solid
pka
12.21±0.60(Predicted)
color 
White
Water Solubility 
11.86g/L(temperature not stated)
Merck 
13,6274
BRN 
48732
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey
QVCMHGGNRFRMAD-XFGHUUIASA-N
LogP
-0.370 (est)
IARC
2B (Vol. 10, Sup 7) 1987
EPA Substance Registry System
Monocrotaline (315-22-0)
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Safety

Hazard Codes 
T
Risk Statements 
25-40-35
Safety Statements 
36/37/39-45
RIDADR 
UN 1544 6.1/PG 3
WGK Germany 
3
RTECS 
QB3140000
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29399990
Hazardous Substances Data
315-22-0(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 71 mg/kg (Newberne)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H351Suspected of causing cancer

Precautionary statements

P201Obtain special instructions before use.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C2401
Product name
Crotaline
Packaging
1g
Price
$512
Updated
2024/03/01
Cayman Chemical
Product number
16666
Product name
Monocrotaline
Purity
≥98%
Packaging
50mg
Price
$62
Updated
2024/03/01
Cayman Chemical
Product number
16666
Product name
Monocrotaline
Purity
≥98%
Packaging
1g
Price
$419
Updated
2024/03/01
Sigma-Aldrich
Product number
PHL89251
Product name
Monocrotaline
Purity
phyproof? Reference Substance
Packaging
20mg
Price
$288
Updated
2024/03/01
Sigma-Aldrich
Product number
C2401
Product name
Crotaline
Packaging
500mg
Price
$297
Updated
2024/03/01
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MONOCROTALINE Chemical Properties,Usage,Production

Description

Monocrotaline (MCT) is a toxic 11-membered macrocyclic pyrrolizidine alkaloid (PA) derived from the seeds of the Crotalaria spectabilis plant. It poisons livestock and humans through the ingestion of contaminated grains and other foods. Pyrrolizidine alkaloid is activated by cytochrome P450 to the reactive pyrrole metabolite dehydromonocrotaline (MCTP) in the liver. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature.
Monocrotaline is produced for research use. It is used in rat model to investigate human pulmonary hypertension as it offers technical simplicity, reproducibility, and low cost compared with other models of pulmonary hypertension.

References

[1] Jose G. Gomez-Arroyo, Laszlo Farkas, Aysar A. Alhussaini, Daniela Farkas, Donatas Kraskauskas, Norbert F. Voelkel, Harm J. Bogaard (2012) The monocrotaline model of pulmonary hypertension in perspective, Am J Physio Lung Cell Mol Phyisol, 302, L363-L369
[2] https://pubchem.ncbi.nlm.nih.gov/compound/monocrotaline#section=Top

Description

A hepatotoxic alkaloid of the pyrrolizidine group obtained from Crotalaria retusa and C. spectabilis, the base is laevorotatory with [α]26D - 55.7° (CHCI3). It may be characterized as the hydrochloride, m.p. 184°C ldec.); [α]28D - 38.4° (H20) and the methiodide which crystallizes from MeOH with 3 moles of solvent, m.p. 205°C (dry, dec.); [α]28D + 23.4° (MeOH). Hydrolysis with boiling Ba(OHh furnishes retronecine and monocrotic acid, C7H120 3, b.p. 145-6°C/ 18 mm which is optically inactive. This acid yields a methyl ester, b.p. 94-6°Cj 18 mm, a p-bromophenacyl ester, m.p. 78°C and a 2:4-dinitrophenylhydrazone, m.p. 95-6°C. Hydrogenation in the presence of Pt02 as catalyst yields retro_x0002_necanol and monocrotalic acid, CSH120S' m.p. 181-2°C; [α]28D - 5.33° (H20) which gives a methyl ester, m.p. 79-800 C; [α]30D - 16.2° (EtOH) and a pbromophenacyl ester, m.p. 162-3°C.

Chemical Properties

White to light tan powder

Physical properties

Appearance: white prism crystal. Solubility: soluble in methanol, ethanol, and chloroform; slightly soluble in benzene, water, ether, and acetone; insoluble in petroleum ether. Melting point: 197–198 °C. Specific optical rotation: ?54.7 ° (in chloroform).

History

In 1935, W.?M. Neil and L.?L. Russoff isolated monocrotaline from Crotalaria sessiliflora L.?Monocrotaline showed anticancer activity in?vivo, especially for treating squamous cell carcinoma, cervical cancer, and leukemia. However, since many pyrrolizidine alkaloid compounds have hepatotoxicity, further development of these compounds is restricted.
China began the research of monocrotaline, as early as 1943. Crotalaria sessiliflora L. was also recorded in the 1977 edition of the Pharmacopoeia of the People’s Republic of China. But monocrotaline was reported for its liver toxicity; teratogenic, allergic reactions; and other side effects, limiting its further clinical applications. In 1992, the Ministry of Health stopped the clinical application of monocrotaline injection. Further pharmacology study is essential for monocrotaline .

Uses

Crotaline has been used in hydrochloric acid (HCl) and injected into experimental animals to induce-pulmonary hypertension.

Uses

A toxic pyrrolizidine alkaloid isolated from Crotalaria spp. It is used for inducing pulmonary diseases in rats.

Uses

antineoplastic, insect sterilant

Definition

ChEBI: Monocrotaline is a pyrrolizidine alkaloid.

Indications

This product is available in the Pharmacopoeia of the People’s Republic of China (1977).
Clinical available formulations include gel and liposome transdermal preparations. It is effective in treating skin cancer, basal cell carcinoma, acute leukemia, and cervical and penile cancer.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Crotaline induces pulmonary vascular syndrome in rats. It is considered toxic and results in hepatic cirrhosis, enlarged liver, sinusoidal obstruction syndrome and right ventricular hypertrophy.

Pharmacology

Monocrotaline is a pyrrolizidine alkaloid which has anticancer and anti-choline effects. In vitro study suggested that monocrotaline has significant cytotoxicity in human BEL-7402, KB cancer cells through inducing DNA alkylation . Monocrotaline’s toxicity is low, but its metabolites in the liver have high liver toxicity. The metabolites are highly electrophilic and can bind to enzymes, proteins, DNA, and RNA, thus causing several side effects. Monocrotaline can reduce blood pressure and inhibit cardiac contractility and heart rate and also shows mild inhibition of respiratory rate and depth.

Clinical Use

Monocrotaline injection shows well therapeutic effect for treating squamous cell carcinoma and basal cell carcinoma. In folk, the fresh pulp or dry powder of the herb has been also used for treating squamous cell carcinoma and basal cell carcinoma .

Safety Profile

Suspected carcinogen with experimental carcinogenic data. Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Crotaline forms prisms from absolute EtOH and recrystallises also from CHCl3. UV in 96% EtOH has max 217nm (log  3.32). [Adams et al. J Am Chem Soc 74 5612 1952, Culvenor & Smith Aust J Chem 10 474 1957.] The hydrochloride has m 212-214o (from MeOH/Et2O) and [] D28 -38.4o (c 5, H2O) [Adams & Gianturco J Am Chem Soc 78 1922 1956]. The picrate has m 230-231.5o(dec) [Adams et al. J Am Chem Soc 74 5614 1952]. [Beilstein 27 III/IV 6660.]

References

Adams, Rogers., J. Amer. Chern. Soc., 61,2815 (1939)

MONOCROTALINE Preparation Products And Raw materials

Raw materials

Preparation Products

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MONOCROTALINE Suppliers

Nanjing Bencao Yikang Biotechnology Co., Ltd
Tel
+86-025-69790911 18362932668
Email
522593521@qq.com
Country
China
ProdList
1163
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58
Chengdu Peter-like Biotechnology Co., Ltd.
Tel
028-81700200 18108052721
Email
2850505130@qq.com
Country
China
ProdList
5177
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58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
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61
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
China DongFan Chemical Co.,LTD
Tel
86-0571-85151182
Fax
86-0571-85151182
Country
China
ProdList
5691
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66
Sichuan Kulinan Technology Co., Ltd
Tel
400-1166-196 18981987031
Fax
028-84555506 800101999
Email
cdhxsj@163.com
Country
China
ProdList
11707
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Hunan Hui Bai Shi Biotechnology Co., Ltd.
Tel
0731-85526065 13308475853
Email
ivy@hnhbsj.com
Country
China
ProdList
4552
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Shenzhen Sungening Bio-Tech Co., Ltd
Tel
+86-0755-89668383
Fax
+86-0755-89594066/4038
Email
sales@sungening.com
Country
China
ProdList
1319
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Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
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View Lastest Price from MONOCROTALINE manufacturers

Shanghai Standard Technology Co., Ltd.
Product
Monocrotaline 315-22-0
Price
US $0.00/mg
Min. Order
5mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2019-12-12
Shaanxi Dideu Medichem Co. Ltd
Product
Monocrotaline 315-22-0
Price
US $0.00-0.00/Kg
Min. Order
1KG
Purity
99.0%
Supply Ability
800 ton
Release date
2020-04-30
Career Henan Chemical Co
Product
MONOCROTALINE 315-22-0
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1kg,5kg,100kg
Release date
2019-07-10

315-22-0, MONOCROTALINERelated Search:


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  • (13-alpha,14-alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
  • (2,3,4-gh)pyrrolizine-2,6(3h)-dione,(4,5,8,10,12,13,13a,13b-octahydro-4,5-dihy
  • (2,3,4-gh)pyrrolizine-2,6(3H)-dione,(4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-
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  • 14,19-Dihydro-12,13-dihydroxy(13alpha,14alpha)-20-norcrotalanan-11,15-dione
  • 14,19-dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione
  • 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13alpha,14alpha)-
  • 20-norcrotalanan-11,15-dione,14,19-dihydro-12,13-dihydroxy-,(13-alpha,14-al
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  • 2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine, 20-norcrotalanan-11,15-dione deriv.
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