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379-79-3

379-79-3 Structure

379-79-3 Structure
IdentificationMore
[Name]

ERGOTAMINE TARTRATE
[CAS]

379-79-3
[Synonyms]

ERGOTAMINE TARTRATE
-,[theta-(theta,theta)]-2,3-dihydroxybutanedioate(2:1)(salt)
6’,18-trione,12’-hydroxy-2’-methyl-5’-(phenylmethyl)-ergotaman-3(5’alpha)
ergam
ergate
ergomar
ergostat
ergotaminebitartrate
ergotartrate
etin
exmigra
femergin
gotaminetartrate
gynergen
lingraine
lingran
neo-ergotin
rigetamin
secagyn
secupan
[EINECS(EC#)]

206-835-9
[Molecular Formula]

C70H76N10O16
[MDL Number]

MFCD08277639
[Molecular Weight]

1313.41
[MOL File]

379-79-3.mol
Chemical PropertiesBack Directory
[Appearance]

Ergotamine tartrate is a crystalline solid.
[Melting point ]

~195 °C (dec.)(lit.)
[alpha ]

D25 -125 to -155° (c = 0.4 in chloroform)
[storage temp. ]

2-8°C
[Merck ]

13,3696
[BRN ]

6173437
[CAS DataBase Reference]

379-79-3(CAS DataBase Reference)
[EPA Substance Registry System]

Ergotamine tartrate (379-79-3)
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R62:Possible risk of impaired fertility.
R63:Possible risk of harm to the unborn child.
[Safety Statements ]

S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

UN 1544 6.1/PG 1
[WGK Germany ]

3
[RTECS ]

KE8225000
[F ]

3-8-10
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29396200
[Safety Profile]

Poison by ingestion, intravenous, and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion: hallucinations, dstorted perceptions, convulsions, nausea or vomiting, blood pressure elevation. Experimental reproductive effects. Human mutation data reported. Used in production of drugs of abuse. When heated to decomposition it emits toxic fumes of NOx. See also ERGOT.
Hazard InformationBack Directory
[General Description]

Powder or liquid forms available as drugs. Used in obstetrics and in the treatment of migraine headaches.
[Reactivity Profile]

ERGOTAMINE TARTRATE(379-79-3) is sensitive to prolonged exposure to heat and light. . When heated to decomposition, ERGOTAMINE TARTRATE(379-79-3) emits toxic fumes of nitrogen oxides. Protect from light and heat [EPA, 1998].
[Air & Water Reactions]

Insoluble in water.
[Health Hazard]

High oral toxicity and a convulsant in humans.People with liver damage are at a greater risk.
[Potential Exposure]

(Toxicity evaluation); Suspected reprotoxic hazard, Suspected of causing genetic defects. The major uses of the ergot alkaloids fall into two categories: applications in obstetrics and treatment of migraine headaches. May be used in the production of “street” drugs
[Fire Hazard]

When heated to decomposition, ERGOTAMINE TARTRATE emits toxic fumes of nitrogen oxides. Protect from light and heat
[First aid]

Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.
[Shipping]

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required
[Incompatibilities]

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, light, and heat
[Description]

Ergotamine and ergometrine belong to two kinds of ergot alkaloids. Ergot (Claviceps purpurea, 麦角) is the sclerotium of ergot fungus that grows in the rye and related cereal and forage plants. The ergot is grown in the northeast and north China and Xinjiang, Jiangsu, Zhejiang, Sichuan, and other places. At present, the method of growth of ergot is inoculation cultivation.
Traditional Chinese medicine believes that ergot is tasteless, tepid, toxic, liver meridian, and kidney meridian. The traditional usage of ergot is oral administration of extractum, 2–4 ml each time, daily amount of 6–8 ml. Its dosage forms also contain infusion, pills, injection, etc. Pharmacology of Chinese Medicine records ergot can be used for uterine contraction, uterine bleeding, and postpartum hemorrhage after delivery, incomplete recovery of uterus, retrogression, etc. The Plateau Chinese herbal medicine treatment manual records that ergot can cure migraine.
[Chemical Properties]

Ergotamine tartrate is a crystalline solid.
[Chemical Properties]

White Solid
[Physical properties]

Appearance: White or slightly yellow fine crystalline powder with slight hygroscopicity. Solubility: Slightly soluble in water and ethanol, insoluble in ether and chloroform.
[History]

As a kind of traditional Chinese medicine, ergot was originally used for hemostasis and involution of uterus by stimulating the uterine muscle powerfully and persistently. After the modernization the traditional Chinese medicine was putting forward, by making several kinds of wild ergot into extractum, we found that all of them can promote the contraction of the rabbit uterus in vivo and in vitro. In isolated rabbit uterus, the effect of ergot on postpartum uterus and pregnant uterus was stronger than nonpregnant uterus. Among a variety of active ingredients in the ergot, ergonovine has the strongest effect on uterine, followed by ergotamine. Seventeen of the 131 strains of ergot derived from the host plants of our country are able to produce ergot alkaloids in wheat culture medium. Among the strains, Claviceps microcephala Ce-3 produces the most ergonovine. Therefore, it became the main bacteria used in the process of industrialization. The study suggested that ergotamine or ergot can block the a-adrenergic receptor, so that the pressor effect of adrenaline was reversed. They do not prevent the release of sympathetic mediators. It showed that the effect of ergotamine is similar to norepinephrine on the hypogastric nerve of guinea pig in vitro. Low dose of ergot can stimulate the brain (slow heart rate, breathing, convulsions, etc.) whereas high dose can cause deaths due to the delayed paralysis. In addition, it can enhance the sedative and hypnotic effects of barbiturates, morphine, and methadone.
[Uses]

Antimigraine.
[Uses]

diuretic, inhibits Na/K/2Cl carrier system
[Indications]

Ergometrine maleate is used in the form of extract tumor injection. As a uterotonic, ergometrine maleate is mainly used for the prevention and treatment of uterine bleeding caused by weak or poor uterine contraction after delivery or abortion, as well as the incomplete recovery of postpartum uterus to accelerate the recovery of uterus.
Ergotamine tartrate is used for the treatment of migraine in the form of tablet and parenteral solution. It also can be used for other neurogenic headache as well.
[Brand name]

Ergomar (Harvest);Ergostat (Parke-Davis); Wigrettes (Organon).
[Pharmacology]

1. The effect of uterus excitation
The effect of ergot on the uterine muscle is similar to the posterior pituitary preparation, which directly acts on the uterine muscle with more powerful and lasting effects. The pregnant uterus is more sensitive to ergot. Low dose of ergot has significant effects on the uterus of labor and new postpartum with severely tetanic contraction. The extracts from several kinds of wild ergot can promote the contraction and increase the tension of uterus in rabbit in vivo and in vitro . Among a variety of active ingredients in the ergot, ergonovine has the strongest effect on uterus, followed by ergotamine.
2. The effects on cardiovascular
In the isolated vascular experiment, ergotamine can cause the contraction of peripheral vascular smooth muscle and hypertension due to vasoconstriction and boost and eventually produce compensatory bradycardia. Ergot has less effect on the heart than blood vessels, but when the heart rate drops to a certain extent, it can enhance the cardiac contractility. High dose of ergotamine can damage vascular endothelial cells (the mechanism is unknown), leading to gangrene. Ergotine has the strongest effect on blood vessels, and ergometrine hardly affects blood pressure and damages to vascular endothelial cells. Ergotine can cause vasoconstriction and decrease the arterial pulse amplitude, which may be related to the therapeutic effect on migraine.
3. The effects on the nervous system
Ergotamine or ergot can block the a-adrenergic receptor and reverse the pressor effect of adrenaline without preventing the release of sympathetic neurotransmitters. Low dose of ergot stimulates the brain (slow down heart rate, breathing, convulsions, etc.), whereas high dose causes deaths due to the delayed paralysis. Ergotamine enhances the sedative and hypnotic effects of barbiturates, morphine, and methadone.
[Clinical Use]

Ergonovine maleate is mainly used for the prevention and treatment of the weak uterine contraction or poor contraction caused by uterine bleeding after delivery or abortion. It is also used for incomplete recovery of postpartum uterus to accelerate the recovery of the uterus.
Ergotamine tartrate is mainly used for the treatment of migraine by relieving the symptoms. However, it is only suitable for short-term usage of headache attacks, normally does not prevent migraine. The combination of ergotamine tartrate and caffeine is better than single oral administration with the mild side effects. It also can be used for other neurogenic headaches.
[Purification Methods]

It crystallises from MeOH. [Beilstein 25 III/IV 964.]
Spectrum DetailBack Directory
[Spectrum Detail]

ERGOTAMINE TARTRATE(379-79-3)IR1
ERGOTAMINE TARTRATE(379-79-3)IR2
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

379-79-3(sigmaaldrich)
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