Synonym
Strychnine; NSC5365; NSC-5365; NSC 5365;
IUPAC/Chemical Name
(4aR,4a1R,5aS,8aR,8a1S,15aS)-2,4a,4a1,5,5a,7,8,8a1,15,15a-decahydro-14H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one
InChi Key
QMGVPVSNSZLJIA-FVWCLLPLSA-N
InChi Code
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
SMILES Code
O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7c6cccc7
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Strychnine is a glycine receptor antagonist not associated with the N-methyl-D-aspartate (NMDA) receptor.
In vitro activity:
The results presented here show that the convulsive alkaloid strychnine reversibly inhibits different subtypes of muscle and neuronal AcChoRs in a noncompetitive manner and with different strengths. In conclusion, our results suggest that strychnine inhibits noncompetitively the function of AcChoRs by interacting at an external site of muscle AcChoRs and by blocking the ion channel in neuronal AcChoRs.
Reference: Proc Natl Acad Sci U S A. 1999 Mar 30;96(7):4113-8. https://pubmed.ncbi.nlm.nih.gov/10097172/
In vivo activity:
Consistent with previous results demonstrating that lateral/basolateral amygdala neurons express functional strychnine-sensitive glycine receptors, microinjection of strychnine (0.5pmol or 167pg) directly into this brain region reduced ‘anxiety-like’ behaviors in two separate assays.
Reference: Behav Brain Res. 2007 Mar 12;178(1):70-81. https://pubmed.ncbi.nlm.nih.gov/17207866/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
334.42
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Dudeck O, Lübben S, Eipper S, Knörle R, Kirsch M, Honegger J, Zentner J, Feuerstein TJ. Evidence for strychnine-sensitive glycine receptors in human amygdala. Naunyn Schmiedebergs Arch Pharmacol. 2003 Sep;368(3):181-7. doi: 10.1007/s00210-003-0786-4. Epub 2003 Aug 16. PMID: 12923611.
2. García-Colunga J, Miledi R. Modulation of nicotinic acetylcholine receptors by strychnine. Proc Natl Acad Sci U S A. 1999 Mar 30;96(7):4113-8. doi: 10.1073/pnas.96.7.4113. PMID: 10097172; PMCID: PMC22429.
3. McCool BA, Chappell A. Strychnine and taurine modulation of amygdala-associated anxiety-like behavior is 'state' dependent. Behav Brain Res. 2007 Mar 12;178(1):70-81. doi: 10.1016/j.bbr.2006.12.002. Epub 2007 Jan 17. PMID: 17207866; PMCID: PMC1839829.
4. Roy NM, Arpie B, Lugo J, Linney E, Levin ED, Cerutti D. Brief embryonic strychnine exposure in zebrafish causes long-term adult behavioral impairment with indications of embryonic synaptic changes. Neurotoxicol Teratol. 2012 Nov-Dec;34(6):587-91. doi: 10.1016/j.ntt.2012.08.001. Epub 2012 Aug 7. PMID: 23022260; PMCID: PMC4338986.
In vitro protocol:
1. Dudeck O, Lübben S, Eipper S, Knörle R, Kirsch M, Honegger J, Zentner J, Feuerstein TJ. Evidence for strychnine-sensitive glycine receptors in human amygdala. Naunyn Schmiedebergs Arch Pharmacol. 2003 Sep;368(3):181-7. doi: 10.1007/s00210-003-0786-4. Epub 2003 Aug 16. PMID: 12923611.
2. García-Colunga J, Miledi R. Modulation of nicotinic acetylcholine receptors by strychnine. Proc Natl Acad Sci U S A. 1999 Mar 30;96(7):4113-8. doi: 10.1073/pnas.96.7.4113. PMID: 10097172; PMCID: PMC22429.
In vivo protocol:
1. McCool BA, Chappell A. Strychnine and taurine modulation of amygdala-associated anxiety-like behavior is 'state' dependent. Behav Brain Res. 2007 Mar 12;178(1):70-81. doi: 10.1016/j.bbr.2006.12.002. Epub 2007 Jan 17. PMID: 17207866; PMCID: PMC1839829.
2. Roy NM, Arpie B, Lugo J, Linney E, Levin ED, Cerutti D. Brief embryonic strychnine exposure in zebrafish causes long-term adult behavioral impairment with indications of embryonic synaptic changes. Neurotoxicol Teratol. 2012 Nov-Dec;34(6):587-91. doi: 10.1016/j.ntt.2012.08.001. Epub 2012 Aug 7. PMID: 23022260; PMCID: PMC4338986.
1: Lee GS, Namkoong G, Park J, Chen DY. Total Synthesis of Strychnine. Chemistry. 2017 Nov 16;23(64):16189-16193. doi: 10.1002/chem.201704455. Epub 2017 Oct 25. PMID: 28940620.
2: Ball CM, Featherstone PJ. Pharmacological treatment of shock-strychnine. Anaesth Intensive Care. 2017 Jan;45(1):3-5. doi: 10.1177/0310057X1704500101. PMID: 28072928.
3: Flood RG. Strychnine poisoning. Pediatr Emerg Care. 1999 Aug;15(4):286-7. PMID: 10460090.
4: Zlotos DP, Mohsen AMY, Mandour YM, Marzouk MA, Breitinger U, Villmann C, Breitinger HG, Sotriffer C, Jensen AA, Holzgrabe U. 11-Aminostrychnine and N-(Strychnine-11-yl)propionamide: Synthesis, Configuration, and Pharmacological Evaluation at Glycine Receptors. J Nat Prod. 2019 Aug 23;82(8):2332-2336. doi: 10.1021/acs.jnatprod.9b00180. Epub 2019 Aug 6. PMID: 31385511.
5: Zheng H, Wang Z, Liu W, Jin H, Zhang J. Toxicokinetics of strychnine and brucine after the oral administration of Biqi capsule to rats by RRLC-MS/MS. Biomed Chromatogr. 2018 Mar;32(3). doi: 10.1002/bmc.4117. Epub 2017 Nov 3. PMID: 29027676.
6: Jackson G, Diggle G. Strychnine-containing tonics. Br Med J. 1973 Apr 21;2(5859):176-7. doi: 10.1136/bmj.2.5859.176-b. PMID: 4699602; PMCID: PMC1589243.
7: Santhosh GJ, Joseph W, Thomas M. Strychnine poisoning. J Assoc Physicians India. 2003 Jul;51:739-40. PMID: 14621058.
8: Prat S, Hoizey G, Lefrancq T, Saint-Martin P. An unusual case of strychnine poisoning. J Forensic Sci. 2015 May;60(3):816-7. doi: 10.1111/1556-4029.12706. Epub 2015 Feb 20. PMID: 25702781.
9: Tomba G, Camilloni C, Vendruscolo M. Determination of the conformational states of strychnine in solution using NMR residual dipolar couplings in a tensor-free approach. Methods. 2018 Sep 15;148:4-8. doi: 10.1016/j.ymeth.2018.07.005. Epub 2018 Jul 21. PMID: 30036639.
10: Beemelmanns C, Reissig HU. Strychnine as Target, Samarium Diiodide as Tool: A Personal Story. Chem Rec. 2015 Oct;15(5):872-85. doi: 10.1002/tcr.201500024. Epub 2015 Jul 29. PMID: 26223366.
