Strychnine

Strychnine
Names
	IUPAC name Strychnidin-10-one
	Systematic IUPAC name (4bR,4b1S,7aS,8aR,8a1R,12aS)-4b1,5,6,7a,8,8a,8a1,11,12a,13-Decahydro-14H-12-oxa-7,14a-diaza-7,9-methanocyclohepta[cd]cyclopenta[g]fluoranthen-14-one
Identifiers
CAS Number	57-24-9 (base) ; 60-41-3 (sulfate) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28973 ;
ChEMBL	ChEMBL227934 ; ChEMBL612118 ; ChEMBL486399 ;
ChemSpider	389877 ;
ECHA InfoCard	100.000.290
IUPHAR/BPS	347;
KEGG	C06522 ;
PubChem CID	441071;
RTECS number	WL2275000;
UNII	H9Y79VD43J (base) ; FA486DV76S (sulfate) ;
UN number	1692
CompTox Dashboard (EPA)	DTXSID6023600 ;
	InChI InChI=1S/C21H22N2O2/c24-18-10-16-19-13-9-17-21(6-7-22(17)11-12(13)5-8-25-16)14-3-1-2-4-15(14)23(18)20(19)21/h1-5,13,16-17,19-20H,6-11H2/t13-,16-,17-,19-,20-,21+/m0/s1 Key: QMGVPVSNSZLJIA-FVWCLLPLSA-N ; InChI=1/C21H22N2O2/c24-18-10-16-19-13-9-17-21(6-7-22(17)11-12(13)5-8-25-16)14-3-1-2-4-15(14)23(18)20(19)21/h1-5,13,16-17,19-20H,6-11H2/t13-,16-,17-,19-,20-,21+/m0/s1 Key: QMGVPVSNSZLJIA-FVWCLLPLBR;
	SMILES O=C7N2c1ccccc1[C@@]64[C@@H]2[C@@H]3[C@@H](OC/C=C5\[C@@H]3C[C@@H]6N(CC4)C5)C7;
Properties
Chemical formula	C21H22N2O2
Molar mass	334.419 g·mol−1
Appearance	White or translucent crystal or crystalline powder; Bitter tasting
Odor	Odorless
Density	1.36 g cm−3
Melting point	270 °C; 518 °F; 543 K
Boiling point	284 to 286 °C; 543 to 547 °F; 557 to 559 K
Solubility in water	0.02% (20°C)
Acidity (pKa)	8.25
Pharmacology
Legal status	BR: Class F4 (Other prohibited substances);
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Extremely toxic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H330, H410
Precautionary statements	P260, P264, P273, P280, P284, P301+P310
NFPA 704 (fire diamond)	4 0 0
Flash point	Non flammable
Autoignition; temperature	Non flammable
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	0.5 mg/kg (dog, oral); 0.5 mg/kg (cat, oral); 2 mg/kg (mouse, oral); 16 mg/kg (rat, oral); 2.35 mg/kg (rat, oral);
LDLo (lowest published)	0.6 mg/kg (rabbit, oral)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.15 mg/m3
REL (Recommended)	TWA 0.15 mg/m3
IDLH (Immediate danger)	3 mg/m3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Strychnine (/ˈstrɪkniːn, -nɪn/, STRIK-neen, -⁠nin, US chiefly /-naɪn/ -⁠nyne)^[6]^[7] is a highly toxic, colorless, bitter, crystalline alkaloid used as a pesticide, particularly for killing small vertebrates such as birds and rodents. Strychnine, when inhaled, swallowed, or absorbed through the eyes or mouth, causes poisoning which results in muscular convulsions and eventually death through asphyxia.^[8] While it is no longer used medicinally, it was used historically in small doses to strengthen muscle contractions, such as a heart^[9] and bowel stimulant^[10] and performance-enhancing drug. The most common source is from the seeds of the Strychnos nux-vomica tree.

^ Retrieved from SciFinder. [May 7, 2018]
^ ^a ^b ^c ^d Cite error: The named reference PGCH was invoked but never defined (see the help page).
^ Everett AJ, Openshaw HT, Smith GF (1957). "The constitution of aspidospermine. Part III. Reactivity at the nitrogen atoms, and biogenetic considerations". Journal of the Chemical Society: 1120–1123. doi:10.1039/JR9570001120. S2CID 94111547.
^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ ^a ^b "Strychnine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Wells JC (2008). Longman Pronunciation Dictionary (3rd ed.). Longman. ISBN 978-1-4058-8118-0.
^ Jones D (2011). Roach P, Setter J, Esling J (eds.). Cambridge English Pronouncing Dictionary (18th ed.). Cambridge University Press. ISBN 978-0-521-15255-6.
^ Sharma RK (2007). "Spinal Poisons". Concise Textbook of Forensic Medicine & Toxicology (2nd ed.). Elsevier. pp. 306–308. ISBN 978-81-312-1145-8.
^ "Dead from Strychnine Overdose". Newark Star-Eagle. 12 July 1915. Retrieved 24 June 2024.
^ Munro J (1914-04-18). "Veronal Poisoning: Case of Recovery from 125 Grains". British Medical Journal. 1 (2781): 854–856. doi:10.1136/bmj.1.2781.854. ISSN 0007-1447. PMC 2300683. PMID 20767090. S2CID 41592291. An attempt was made to administer a soap-and-water enema, but the sphincter was not acting. After hypodermic injection of 1/45 grain [1.44 mg] strychnine, a second attempt was made, and a good evacuation of the bowel followed, after which half a pint [284 ml] of normal saline was injected and retained. [...] We decided to adhere to the treatment already commenced – namely, periodical rectal injection of saline and withdrawals of urine by catheter, with oxygen inhalation for cyanosis, and strychnine hypodermically as the pulse weakened.

[1] Retrieved from SciFinder. [May 7, 2018]

[PGCH-2] Cite error: The named reference PGCH was invoked but never defined (see the help page).

[Everett1957-3] Everett AJ, Openshaw HT, Smith GF (1957). "The constitution of aspidospermine. Part III. Reactivity at the nitrogen atoms, and biogenetic considerations". Journal of the Chemical Society: 1120–1123. doi:10.1039/JR9570001120. S2CID 94111547.

[4] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[IDLH-5] "Strychnine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[6] Wells JC (2008). Longman Pronunciation Dictionary (3rd ed.). Longman. ISBN 978-1-4058-8118-0.

[7] Jones D (2011). Roach P, Setter J, Esling J (eds.). Cambridge English Pronouncing Dictionary (18th ed.). Cambridge University Press. ISBN 978-0-521-15255-6.

[sharma-8] Sharma RK (2007). "Spinal Poisons". Concise Textbook of Forensic Medicine & Toxicology (2nd ed.). Elsevier. pp. 306–308. ISBN 978-81-312-1145-8.

[9] "Dead from Strychnine Overdose". Newark Star-Eagle. 12 July 1915. Retrieved 24 June 2024.

[10] Munro J (1914-04-18). "Veronal Poisoning: Case of Recovery from 125 Grains". British Medical Journal. 1 (2781): 854–856. doi:10.1136/bmj.1.2781.854. ISSN 0007-1447. PMC 2300683. PMID 20767090. S2CID 41592291. An attempt was made to administer a soap-and-water enema, but the sphincter was not acting. After hypodermic injection of 1/45 grain [1.44 mg] strychnine, a second attempt was made, and a good evacuation of the bowel followed, after which half a pint [284 ml] of normal saline was injected and retained. [...] We decided to adhere to the treatment already commenced – namely, periodical rectal injection of saline and withdrawals of urine by catheter, with oxygen inhalation for cyanosis, and strychnine hypodermically as the pulse weakened.

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Names


IUPAC name Strychnidin-10-one^[1]
Systematic IUPAC name (4bR,4b¹S,7aS,8aR,8a¹R,12aS)-4b¹,5,6,7a,8,8a,8a¹,11,12a,13-Decahydro-14H-12-oxa-7,14a-diaza-7,9-methanocyclohepta[cd]cyclopenta[g]fluoranthen-14-one
Identifiers
CAS Number	57-24-9 (base)^Y 60-41-3 (sulfate)^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28973^Y
ChEMBL	ChEMBL227934^Y ChEMBL612118^Y ChEMBL486399^Y
ChemSpider	389877^Y
ECHA InfoCard	100.000.290
IUPHAR/BPS	347
KEGG	C06522^Y
PubChem CID	441071
RTECS number	WL2275000
UNII	H9Y79VD43J (base)^Y FA486DV76S (sulfate)^Y
UN number	1692
CompTox Dashboard (EPA)	DTXSID6023600
InChI InChI=1S/C21H22N2O2/c24-18-10-16-19-13-9-17-21(6-7-22(17)11-12(13)5-8-25-16)14-3-1-2-4-15(14)23(18)20(19)21/h1-5,13,16-17,19-20H,6-11H2/t13-,16-,17-,19-,20-,21+/m0/s1^Y Key: QMGVPVSNSZLJIA-FVWCLLPLSA-N^Y InChI=1/C21H22N2O2/c24-18-10-16-19-13-9-17-21(6-7-22(17)11-12(13)5-8-25-16)14-3-1-2-4-15(14)23(18)20(19)21/h1-5,13,16-17,19-20H,6-11H2/t13-,16-,17-,19-,20-,21+/m0/s1 Key: QMGVPVSNSZLJIA-FVWCLLPLBR
SMILES O=C7N2c1ccccc1[C@@]64[C@@H]2[C@@H]3[C@@H](OC/C=C5\[C@@H]3C[C@@H]6N(CC4)C5)C7
Properties
Chemical formula	C₂₁H₂₂N₂O₂
Molar mass	334.419 g·mol⁻¹
Appearance	White or translucent crystal or crystalline powder; Bitter tasting
Odor	Odorless
Density	1.36 g cm⁻³
Melting point	270 °C; 518 °F; 543 K
Boiling point	284 to 286 °C; 543 to 547 °F; 557 to 559 K
Solubility in water	0.02% (20°C)^[2]
Acidity (pK_a)	8.25^[3]
Pharmacology
Legal status	BR: Class F4 (Other prohibited substances)^[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Extremely toxic
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H330, H410
Precautionary statements	P260, P264, P273, P280, P284, P301+P310
NFPA 704 (fire diamond)	4 0 0
Flash point	Non flammable
Autoignition temperature	Non flammable
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	0.5 mg/kg (dog, oral) 0.5 mg/kg (cat, oral) 2 mg/kg (mouse, oral) 16 mg/kg (rat, oral) 2.35 mg/kg (rat, oral)^[5]
LD_Lo (lowest published)	0.6 mg/kg (rabbit, oral)^[5]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.15 mg/m³^[2]
REL (Recommended)	TWA 0.15 mg/m³^[2]
IDLH (Immediate danger)	3 mg/m³^[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references