HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

Strychnin

HCID 5304
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
57-24-9
Standard SMILES
O=C1CC2OCC=C3CN4CCC56c7ccccc7N1C5C2C3CC46
InChIKey
QMGVPVSNSZLJIA-UHFFFAOYSA-N
Molecular formula
C21H22N2O2
Average molar mass
334.4 g/mol
Monoisotopic mass
334.16812795

Overview

strychnidine-14-one (unspec. stereochem.) has been reported in Strychnos nux-vomica with data available.

Names & identifiers

Preferred name
Strychnin
IUPAC
4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one
English name
STRYCHNINE
Molecular formula
C21H22N2O2
Molecular weight
334.41

Names & synonyms

Strychnin4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo(3,2,1-ij)oxepino(2,3,4-de)pyrrolo(2,3-h)quinolin-14-one4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-oneRefChem:1099105NSC5365VauqulineNSC 5365CHEMBL1609139SCHEMBL29362678QMGVPVSNSZLJIA-UHFFFAOYSA-NMFCD00005941STL372869
Show more names
(-)-STRYCHNINEnuxvomicastrychineStrychnidin-10-oneCertoxKwik-Kilhare-ridSanaseedmoledeath
AKOS025247982UN 1692NCGC00167847-01VS-12360DB-050083WLN: T6 G656 B7 C6 E5 D 5ABCEF A& FX MNV QO VN SU AHT&&TTTTJ12-oxa-8,17-diazaheptacyclo[15.5.2.0(1),(1)?.0(2),?.0?,(2)(2).0(1)(1),(2)(1).0(1)?,(2)?]tetracosa-2(7),3,5,14-tetraen-9-one

Database identifiers

Properties

Computed structural properties

XLogP
1.9
Topological polar surface area
32.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
25
Formal charge
0
Complexity
689

Physicochemical properties

Melting point
284 · 284-286 °C(lit.)
alpha
18 · D18 -104.3° (c = 0.254 in alc); D25 -139° (c = 0.4 in chloroform)
Boiling point
471.21 °C · 471.21°C (rough estimate)
Density
18 · d18 1.359
vapor pressure
1.5 xl0-7 · 1.5 xl0-7 Pa (20 °C, est.)
refractive index
1.65 · 1.6500 (estimate)
storage temp.
Poison room
solubility
chloroform: clear to hazy
pka
8.26 · 8.26(at 25℃)
Water Solubility
143 mg · 143 mg l-1
form
Fine Crystalline Powder
color
White
Odor
Odorless
Merck
14 · 14,8855
Henry's Law Constant
1.6 · 1.6×108 mol/(m3Pa) at 25℃, HSDB (2015)
Exposure limits

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Treatment · 1 item

Treatment of strychnine poisoning involves an oral application of an activated charcoal infusion to absorb any poison within the digestive tract that has not yet been absorbed into the blood. Anticonvulsants such as phenobarbital or diazepam are administered to control convulsions, along with muscle relaxants such as dantrolene to combat muscle rigidity. (L1228)

Health EffectsDeath may result from asphyxia or sheer exhaustion. (L1230)
Exposure RoutesOral (ingestion) (L1817) ; dermal (L1817)
Toxicity SummaryStrychnine acts as an antagonist at the inhibitory or strychnine-sensitive glycine receptor, a ligand-gated chloride channel in the spinal cord and the brain. (L1230)
Signs and SymptomsStrychnine causes muscular convulsions of increasing intensity and frequency and eventually death through asphyxia or sheer exhaustion. (L1230)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: 2350 ug/kg (Oral, Rat) (T14) LD50: 1100 ug/kg (Intraperitoneal, Rat) (T14) LD50: 1200 ug/kg (Subcutaneous, Rat) (T14) LD50: 582 ug/kg (Intravenous, Rat) (T14)

Safety data

OEB
C
OEL
TWA: 0.15 mg/m3
wgk
3
IDLA
3 mg/m3
tsca
TSCA listed
rtecs
WL2275000

Chemistry & industry

Uses & manufacturing

UsesStrychnine is a plant toxin most commonly found in the seeds of the Strychnine tree (Strychnos nux-vomica L.). It is used as a pesticide, particularly for killing small vertebrates such as birds and rodents. (L1230)
Applications · 8 items

DescriptionStrychnine, C21H22N2O2, Mr 334.4, mp 270–280 C (decomp.), forms colorless crystals which are slightly soluble in water, moderately in benzene, ethanol, readily soluble in chloroform [9, p. 1121].

HistoryStrychnine is a white, odorless, toxic crystalline powder with a bitter taste. Strychnine is a well-known poison, but it has also been used in medications. It was one of the first alkaloids to be isolated in pure form when Joseph Bienaimé Caventou (1795 1877) and Pierre Joseph Pelletier (1788 1842) extracted it from Saint Ignatius beans (Strychnos ignatii) in 1818. Caventou and Pelletier subsequently obtained it from its main source Strychnos nux vomica; it is also found in other Strychnos species. Strychnos nux vomica is an evergreen tree native to east India, Southeast Asia, and northern Australia. The seeds of the plant are the main source of strychnine and several other alkaloids (brucine), but it is also obtained from the bark and roots. The seeds are heated and then ground to a powder that contains strychnine. The brownish-gray powder obtained from the ground seeds extracted from the nut is called nux vomica. In commercial production during the 1800s, the seeds were softened by boiling in a dilute sulfuric acid solution and then dried and ground to a powder. Strychnine was extracted from the powder using alcohol and separation techniques to remove impurities. The structure of strychnine was determined by Robert Robinson (1886 1975) in 1946; the next year Robinson received the Nobel Prize in chemistry for his work on alkaloids. Robert Burns Woodward (1917 1979) performed the first complete synthesis of strychnine in 1953.Strychnine was used in its impure powder form centuries before it was isolated. The nuts that yielded the seeds were given names such as poison nut or vomit nuts. Early workers on its properties warned about its poisonous properties and recommended against it internal use.

UsesStrychnine as nux vomica was available in apothecaries throughoutthe 19th century, and strychnine salts such as strychnine sulfate, strychnine nitrate, andstrychnine phosphate were a popular medicine. It was sold as pills, powders, and tinctures.Small quantities of strychnine were added to tonics to serve as stimulants. Because its bittertaste stimulates saliva and gastric production, strychnine was used to counteract the lossof appetite produced by various diseases. Hypodermic injections of strychnine along withdigitalis were prescribed for treating acute heart failure in the early 20th century. Otherconditions for which strychnine was prescribed included paralysis, impotence, alcoholism,and drug addiction.Today strychnine as nux vomica is still available as an herbal ingredient for herbal and homeopathic remedies. The action of nux vomica is attributed to strychnine and brucine. It is recommended for stomach ailments such as atonic dyspepsia, constipation, heart burn, and indigestion. It is reported to relieve nausea during pregnancy. Chinese herbalists use nux vomica externally to treat tumors, headaches, and paralysis. It is recommended for the treatment of Bell's palsy. Strychnine has some uses in modern traditional medicine. It has been used to treat the genetic disorder nonketotic hyperglycinaemia (NKH). NKH is related to glycine metabolism; it can lead to high levels of the inhibitory receptor glycine resulting in seizures. Strychnine is used in neurological research by applying it to areas of the brain or spinal column and observing how the nervous system responds. This method is called strychnine neuronography. Strychnine has been used in conjunction with antivenoms to treat poisonous snake bites. Strychnine is sometimes cut into cocaine, heroin, and other illegal substances in the production of designer drugs. Strychnine was once used liberally as a pesticide, especially to control vertebrates.It is used as a salt in granular bait formulations. In the United States its use has been progressively limited over the years. . In the1980s, its use was curtailed for above-ground applications to reduce toxicity to nontargetspecies, especially birds; by the end of the decade, its use was limited to below ground.Currently, strychnine is only registered for use by the EPA as a below-ground bait pesticidefor use on pocket gophers.

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS
57-24-9
PubChem CID
5304
ChEMBL
CHEMBL1609139
0.15 mg/m3OSHA:PEL-TWA · ACGIH:TLV-TWA 0.15 mg/m3OSHA:PEL-TWA 0.15 mg/m3NIOSH:REL-TWA 0.15 mg/m3
Stability
Stable. Incompatible with strong oxidizing agents.
LogP
1.93 · 1.930
CAS DataBase Reference
57 · 57-24-9(CAS DataBase Reference)
FDA 21 CFR
310.545 · 310.545
EWG's Food Scores
1 · 1-5
FDA UNII
9 Y79VD43J · H9Y79VD43J
Pesticides Freedom of Information Act (FOIA)
Strychnine
EPA Substance Registry System
Strychnine (57-24-9)
Symbol(GHS)
6 · GHS06,GHS09
Signal word
Danger
Hazard statements
300 · H300+H310-H410
Precautionary statements
262 · P262-P264-P273-P280-P301+P310-P302+P352+P310
Hazard Codes
T+,N
Risk Statements
27 · 27/28-50/53
Safety Statements
36 · 36/37-45-60-61
RIDADR
1692 · UN 1692 (STRYCHNINE or STRYCHNINE SALTS)
OEB
C
OEL
0.15 mg/m3 · TWA: 0.15 mg/m3
WGK Germany
3 · 3
RTECS
2275000 · WL2275000
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
I
HS Code
29349990 · 29349990
Hazardous Substances Data
57 · 57-24-9(Hazardous Substances Data)
Toxicity
50 i.v · LD50 i.v. (slow infusion) in rats: 0.96 mg/kg (Setnikar, Magistretti)
IDLA
3 mg/m3 · 3 mg/m3
ridadr
UN 1692 (STRYCHNINE or STRYCHNINE SALTS)
hs_code
29349990
Toxicity
LD50 i.v. (slow infusion) in rats: 0.96 mg/kg (Setnikar, Magistretti)
risk_code
27/28-50/53
Signal word
Danger
Symbol(GHS)
GHS06,GHS09
hazard_code
T+,N
safety_code
36/37-45-60-61
hazard_class
6.1
packing_group
I
Hazard statements
H300+H310-H410
Precautionary statements
P262-P264-P273-P280-P301+P310-P302+P352+P310
Hazardous Substances Data
57-24-9(Hazardous Substances Data)

UsesStrychnine occurs in the seeds of strychnosspecies (S. nux vomica L., S. Loganiaceae,and S. ignatii Berg). The total alkaloid con tent in these plants is 2–3%. The composition of strychnine in these species rangesbetween 1% and 3%. Strychnine is widelyknown as a poison. Its therapeutic applica tions are very limited. It is used as a rodentpoison.

UsesStrychnine is used for the control of moles, squirrels, rabbits, gophers, mice and other small rodents and of bird pests. Rats normally avoid the bait.

UsesDestroying rodents and predatory animals.

Usescentral stimulant

General DescriptionColorless, transparent crystals or white crystalline powder. Has no odor. Used for destroying rodents and predatory animals and for trapping fur-bearing animals.

Upstream & downstream products

Upstream raw materials

12H-1,12-Ethano-9H-pyrido[1,2,3-lm]pyrrolo[2,3-d]carbazol-9-one, 2,3,10,11b,13,13a-hexahydro-14-(2-hydroxyethylidene)-, (1S,3aR,11bS,12S,13aS,14E)-Wieland-Gumlich aldehydeBenzenesulfonamide, N-(2-bromophenyl)-4-methyl-SEMEN STRYCHNIStrychnos extract
Additional notes · 2 items

DefinitionChEBI: Strychnine is a monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position. It has a role as an avicide, a glycine receptor antagonist, a cholinergic antagonist, a rodenticide and a neurotransmitter agent. It is a monoterpenoid indole alkaloid and an organic heteroheptacyclic compound. It is a conjugate base of a strychnine(1+). It derives from a hydride of a strychnidine.

Definitionstrychnine: A colourless poisonouscrystalline alkaloid found in certainplants.