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MedKoo Cat#: 464350 | Name: Hodgkinsine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Hodgkinsine is a pyrrolidinoindoline alkaloid that has been found in P. colorata and has analgesic activity. It increases latency to paw licking in the hot plate test and latency to tail withdrawal in the tail-flick test in mice when administered at a dose of 5 mg/kg.

Chemical Structure

Hodgkinsine
Hodgkinsine
CAS#18210-71-4

Theoretical Analysis

MedKoo Cat#: 464350

Name: Hodgkinsine

CAS#: 18210-71-4

Chemical Formula: C33H38N6

Exact Mass: 518.3158

Molecular Weight: 518.71

Elemental Analysis: C, 76.41; H, 7.38; N, 16.20

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Synonym
Hodgkinsine; (–)-Hodgkinsine; (–) Hodgkinsine;
IUPAC/Chemical Name
(3aS,3'aR,3''aR,8aS,8'aR,8''aR)-1,1',1''-trimethyl-2,2',2'',3,3',3'',8,8a,8',8'a,8'',8''a-dodecahydro-1H,1'H,1''H-3a,3'a:7',3''a-terpyrrolo[2,3-b]indole
InChi Key
DPVWJPVYOXKFRQ-BDMNMGLZSA-N
InChi Code
InChI=1S/C33H38N6/c1-37-18-15-31(21-9-4-6-13-25(21)34-28(31)37)23-11-8-12-24-27(23)36-30-33(24,17-20-39(30)3)32-16-19-38(2)29(32)35-26-14-7-5-10-22(26)32/h4-14,28-30,34-36H,15-20H2,1-3H3/t28-,29+,30-,31-,32-,33+/m1/s1
SMILES Code
CN1[C@@]2([C@@]([C@]34C5=CC=CC=C5N[C@]3(N(C)CC4)[H])(C6=CC=CC([C@@]78C9=CC=CC=C9N[C@@]7(N(C)CC8)[H])=C6N2)CC1)[H]
Appearance
Solid powder
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
>2 years if stored properly
Drug Formulation
To be determined
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
An alkaloid with analgesic activity.
In vitro activity:
TBD
In vivo activity:
Hodgkinsine shows a potent dose-dependent analgesic activity against capsaicin-induced pain, indicating the participation of NMDA receptors in hodgkinsine-induced analgesia. Reference: Planta Med. 2000 Dec;66(8):770-2. https://pubmed.ncbi.nlm.nih.gov/11199142/

Preparing Stock Solutions

The following data is based on the product molecular weight 518.71 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.

Recalculate based on batch purity %
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. Amador TA, Verotta L, Nunes DS, Elisabetsky E. Antinociceptive profile of hodgkinsine. Planta Med. 2000 Dec;66(8):770-2. doi: 10.1055/s-2000-9604. PMID: 11199142.
In vitro protocol:
TBD
In vivo protocol:
1. Amador TA, Verotta L, Nunes DS, Elisabetsky E. Antinociceptive profile of hodgkinsine. Planta Med. 2000 Dec;66(8):770-2. doi: 10.1055/s-2000-9604. PMID: 11199142.
1: Jamison CR, Badillo JJ, Lipshultz JM, Comito RJ, MacMillan DWC. Catalyst- controlled oligomerization for the collective synthesis of polypyrroloindoline natural products. Nat Chem. 2017 Dec;9(12):1165-1169. doi: 10.1038/nchem.2825. Epub 2017 Jul 24. PMID: 29168485. 2: Lindovska P, Movassaghi M. Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines. J Am Chem Soc. 2017 Dec 6;139(48):17590-17596. doi: 10.1021/jacs.7b09929. Epub 2017 Nov 20. PMID: 29058431; PMCID: PMC5733798. 3: Snell RH, Durbin MJ, Woodward RL, Willis MC. Catalytic enantioselective desymmetrisation as a tool for the synthesis of hodgkinsine and hodgkinsine B. Chemistry. 2012 Dec 21;18(52):16754-64. doi: 10.1002/chem.201203150. Epub 2012 Nov 30. PMID: 23203932. 4: Snell RH, Woodward RL, Willis MC. Catalytic enantioselective total synthesis of hodgkinsine B. Angew Chem Int Ed Engl. 2011 Sep 19;50(39):9116-9. doi: 10.1002/anie.201103864. Epub 2011 Aug 24. PMID: 21919143. 5: Kodanko JJ, Hiebert S, Peterson EA, Sung L, Overman LE, de Moura Linck V, Goerck GC, Amador TA, Leal MB, Elisabetsky E. Synthesis of all low-energy stereoisomers of the tris(pyrrolidinoindoline) alkaloid hodgkinsine and preliminary assessment of their antinociceptive activity. J Org Chem. 2007 Oct 12;72(21):7909-14. doi: 10.1021/jo7013643. Epub 2007 Sep 21. PMID: 17887704. 6: Kodanko JJ, Overman LE. Enantioselective total syntheses of the cyclotryptamine alkaloids hodgkinsine and hodgkinsine B. Angew Chem Int Ed Engl. 2003 Jun 6;42(22):2528-31. doi: 10.1002/anie.200351261. PMID: 12800178. 7: Verotta L, Orsini F, Sbacchi M, Scheildler MA, Amador TA, Elisabetsky E. Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-type alkaloids. Bioorg Med Chem. 2002 Jul;10(7):2133-42. doi: 10.1016/s0968-0896(02)00078-0. PMID: 11983509. 8: Amador TA, Verotta L, Nunes DS, Elisabetsky E. Antinociceptive profile of hodgkinsine. Planta Med. 2000 Dec;66(8):770-2. doi: 10.1055/s-2000-9604. PMID: 11199142. 9: Jannic V, Guéritte F, Laprévote O, Serani L, Martin MT, Sévenet T, Potier P. Pyrrolidinoindoline alkaloids from Psychotria oleoides and Psychotria lyciiflora. J Nat Prod. 1999 Jun;62(6):838-43. doi: 10.1021/np9805387. PMID: 10395499. 10: Verotta L, Pilati T, Tatò M, Elisabetsky E, Amador TA, Nunes DS. Pyrrolidinoindoline Alkaloids from Psychotria colorata1. J Nat Prod. 1998 Mar 27;61(3):392-6. doi: 10.1021/np9701642. PMID: 9548883. 11: Saad HE, el-Sharkawy SH, Shier WT. Biological activities of pyrrolidinoindoline alkaloids from Calycodendron milnei. Planta Med. 1995 Aug;61(4):313-6. doi: 10.1055/s-2006-958090. PMID: 7480176. 12: Guéritte-Voegelein F, Sévenet T, Pusset J, Adeline MT, Gillet B, Beloeil JC, Guénard D, Potier P, Rasolonjanahary R, Kordon C. Alkaloids from Psychotria oleoides with activity on growth hormone release. J Nat Prod. 1992 Jul;55(7):923-30. doi: 10.1021/np50085a012. PMID: 1402957.

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