pseudopelletierine
{{short description|Chemical compound}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424798005
| ImageFile = pseudopelletierine.png
| ImageSize = 120px
| IUPACName = 9-Methyl-9-azabicyclo[3.3.1]nonan-3-one
| OtherNames = Pseudopunicine; Granatonine; Pseudopelletrierin; Granatan-3-one; Pseudopelletierin; psi-Pelletierine; 9-Methyl-3-granatanone
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 552-70-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = USN3FV3Z9X
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 8607
| PubChem = 11096
| SMILES = CN1C2CCCC1CC(=O)C2
}}
|Section2={{Chembox Properties
| C=9 | H=15 | N=1 | O=1
| Appearance = Colorless (yellows on exposure)
| Density =
| MeltingPtC = 54
| BoilingPt = Sublimes at 40 °C (0.3 mmHg)
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
Pseudopelletierine is the main alkaloid derived from the root-bark of the pomegranate tree (Punica granatum), along with at least three other alkaloids: pelletierine, isopelletierine, and methylpelletierine (C9H17ON), which yield 1.8, 0.52, 0.01, and 0.20 grams per kilogram of raw bark.
It is a homolog of tropinone, and can be synthesized in a manner analogous to the classical Robinson tropinone synthesis, using glutaraldehyde (rather than succinaldehyde), acetonedicarboxylic acid, and methylammonium chloride.{{cite journal|journal=Organic Syntheses|volume= 37|page=73|year=1957|doi=10.15227/orgsyn.037.0073|title=Pseudopelletierine|author=Arthur C. Cope |author2=Hugh L. Dryden Jr. |author3=Charles F. Howell }} It was the starting material for Willstätter's 10-step synthesis of cyclooctatetraene, which was achieved after oxidation and several Hoffman elimination steps.