Ammodendrine

• CAS: 494-15-5
• Catalog Number: ACM494155
• Category: Other Products
• Molecular Weight: 208.3
• Molecular Formula: C₁₂H₂₀N₂O
• Synonyms: (+)-1-Acetyl-1,2,3,4-tetrahydro-5-[(R)-2β-piperidinyl]pyridine
• IUPAC Name: 1-[5-[(2R)-piperidin-2-yl]-3,4-dihydro-2H-pyridin-1-yl]ethanone
• InChI: InChI=1S/C12H20N2O/c1-10(15)14-8-4-5-11(9-14)12-6-2-3-7-13-12/h9,12-13H,2-8H2,1H3/t12-/m1/s1
• InChI Key: APKLQIQRPUDADG-GFCCVEGCSA-N
• Melting Point: 73-74 °C
• Complexity: 273
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Exact Mass: 208.157563266
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Heavy Atom Count: 15
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• Isomeric SMILES: CC(=O)N1CCCC(=C1)[C@H]2CCCCN2
• Monoisotopic Mass: 208.157563266
• Physical State: Powder
• Rotatable Bond Count: 1
• Topological Polar Surface Area: 32.3 Ų

Case Study

Effects of Ammodendrine Alkaloid Teratogen on Fetal Nicotinic Acetylcholine Receptors

Green, Benedict T., et al. Neurotoxicology and teratology, 2010, 32(3), 383-390.

Ammodendrine is one of the teratogenic alkaloids found in plants. The pharmacodynamics of several teratogenic alkaloids, including Ammodendrine, were studied in SH-SY5Y cells and TE-671 cells. Results indicate that these teratogenic alkaloids are more effective in initiating responses and desensitizing TE-671 cells expressing human fetal muscle nAChR than SH-SY5Y cells expressing human autonomous nAChR. The mechanism behind the teratogenic potential of these compounds is stimulation of muscle-type nAChRs, followed by desensitization and finally inhibition of fetal movement.
Ammodendrine related research results
· Ammodendrine was tested in both cell lines. In TE-671 cells, ammodendrine had EC50s of 539 μM and 1101 μM for the racemate and the (+)-enantiomer of ammodendrine. (-)-ammo- dendrine was without effect in TE-671 cells so an EC50 was not calculated. In SH-SY5Y cells, all forms of ammodendrine were of low potency and efficacy. In TE-671 cell line, the ammodendrine compounds were very weak agonists and had only minimal activity at 100 and 1000 μM.
· The rank order of alkaloid EC50 values in TE-671 cells was: anabaseine> (+)-anabasine> (-)-anabasine> (±)-anabasine> anagyrine> (-)-coniine > (±)-coniine> (+)-coniine> (±)-ammodendrine>(+)-ammodendrine.
· The rank order of alkaloid EC50 values in SH-SY5Y cells was: anabaseine>(+)-anabasine>(-)-coniine > (+)- coniine > (+)-ammodendrine > anagyrine> (-)-anabasine > (±)- coniine > (±)-anabasine > (-)-ammodendrine.

Custom Q&A

What is the molecular formula of ammodendrine?

The molecular formula of ammodendrine is C12H20N2O.

What is the molecular weight of ammodendrine?

The molecular weight of ammodendrine is 208.3.

What is the boiling point of ammodendrine?

The boiling point of ammodendrine is 175-186 °C at a pressure of 8-9 Torr.

What is the density of ammodendrine?

The density of ammodendrine is 1.061±0.06 g/cm3 (predicted).

What is the melting point of ammodendrine?

The melting point of ammodendrine is 73-74 °C.

What is the pKa value of ammodendrine?

The pKa value of ammodendrine is 10.29±0.10 (predicted).

How is ammodendrine defined in ChEBI?

Ammodendrine is defined in ChEBI as a piperidine alkaloid that is piperidine substituted by a 1-acetyl-1,4,5,6-tetrahydropyridin-3-yl group at position 2 (the 2R-stereoisomer).

What role does ammodendrine have as per its definition in ChEBI?

Ammodendrine has a role as a plant metabolite and a teratogenic agent according to its definition in ChEBI.

What category does ammodendrine belong to chemically?

Ammodendrine is categorized as a piperidine alkaloid, a N-acylpiperidine, and a member of acetamides.

What are the synonyms for ammodendrine?

Some synonyms for ammodendrine include ammodendrine, (+)-1-Acetyl-1,2,3,4-tetrahydro-5-[(R)-2β-piperidinyl]pyridine, 1-Acetyl-3-[(R)-2-piperidinyl]-1,4,5,6-tetrahydropyridine, D-Ammodendrine, Isoammodendrine, and Ethanone, 1-[3,4-dihydro-5-(2R)-2-piperidinyl-1(2H)-pyridinyl]-.