Hamayne

Hamayne
Names
	Systematic IUPAC name (3α,11R,13β)-1,2-Didehydrocrinan-3,11-diol
	Other names Bulbispermine
Identifiers
CAS Number	61948-11-6 [ EPA ];
3D model (JSmol)	Interactive image ;
ChEBI	CHEBI:31667 ;
ChEMBL	ChEMBL3916492 ;
ChemSpider	23327027 ;
KEGG	C12164 ;
PubChem CID	443670 ;
CompTox Dashboard (EPA)	DTXSID90332125 ;
	InChI InChI=1S/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14-,15-,16+/m0/s1 Key: KWAOMPWGIIXDPH-BLQKSXIESA-N; InChI=1/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14-,15-,16+/m0/s1 Key: KWAOMPWGIIXDPH-BLQKSXIEBO;
	SMILES C1[C@H](C=C[C@@]23[C@H]1N(C[C@@H]2O)CC4=CC5=C(C=C34)OCO5)O;
Properties
Chemical formula	C16H17NO4
Molar mass	287.315 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Last updated May 21, 2025

Hamayne is an alkaloid present in plants of the family Amaryllidaceae, including Iberian Narcissus species and two Nigerian Crinum species, reported to have acetylcholinesterase inhibitory activity.^[1] The product has been made via total synthesis as well.^[2]

References

↑ López, Susana; Bastida, Jaume; Viladomat, Francesc; Codina, Carles (2002). "Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts". Life Sciences. 71 (21): 2521–2529. doi:10.1016/S0024-3205(02)02034-9. PMID 12270757.
↑ Petit, Laurent; Banwell, Martin G.; Willis, Anthony C. (2011). "The Total Synthesis of the Crinine Alkaloid Hamayne via a Pd[0]-Catalyzed Intramolecular Alder-Ene Reaction". Organic Letters. 13 (21): 5800–5803. doi:10.1021/ol2023938. PMID 21970722.

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[1] López, Susana; Bastida, Jaume; Viladomat, Francesc; Codina, Carles (2002). "Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts". Life Sciences. 71 (21): 2521–2529. doi:10.1016/S0024-3205(02)02034-9. PMID 12270757.

[2] Petit, Laurent; Banwell, Martin G.; Willis, Anthony C. (2011). "The Total Synthesis of the Crinine Alkaloid Hamayne via a Pd[0]-Catalyzed Intramolecular Alder-Ene Reaction". Organic Letters. 13 (21): 5800–5803. doi:10.1021/ol2023938. PMID 21970722.

[1]

[2]

Names

Systematic IUPAC name (3α,11R,13β)-1,2-Didehydrocrinan-3,11-diol
Other names Bulbispermine
Identifiers
CAS Number	61948-11-6 ^{N[ EPA ]}
3D model (JSmol)	Interactive image
ChEBI	CHEBI:31667
ChEMBL	ChEMBL3916492
ChemSpider	23327027
KEGG	C12164
PubChem CID	443670
CompTox Dashboard (EPA)	DTXSID90332125
InChI InChI=1S/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14-,15-,16+/m0/s1 Key: KWAOMPWGIIXDPH-BLQKSXIESA-N InChI=1/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14-,15-,16+/m0/s1 Key: KWAOMPWGIIXDPH-BLQKSXIEBO
SMILES C1[C@H](C=C[C@@]23[C@H]1N(C[C@@H]2O)CC4=CC5=C(C=C34)OCO5)O
Properties
Chemical formula	C₁₆H₁₇NO₄
Molar mass	287.315 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references