JavaScript is disabled in your browser. Please enable JavaScript to view this website.
AB144652

Nonivamide, TRPV1 agonist

Be the first to review this product! Submit a review

|

(0 Publication)

MW 293.4 Da, Purity >98%. TRPV1 agonist. Less potent Capsaicin (ab141000) analog. Induces Ca2+ release from ER. Blood-brain barrier permeable. Active in vivo.

View Alternative Names

(R)-limonene 6-monooxygenase, (S)-limonene 6-monooxygenase, (S)-limonene 7-monooxygenase, 1,8-cineole 2-exo-monooxygenase, 15 LIPOXYGENASE RETICULOCYTE ARACHIDONATE, 15 LOX 1, 15 lipoxygenase 1, 15-LOX, ACLS, AIS, ALOX15, ANDR_HUMAN, AR, AR8, Albendazole monooxygenase, Albendazole sulfoxidase, Androgen nuclear receptor variant 2, Androgen receptor, Androgen receptor (dihydrotestosterone receptor; testicular feminization; spinal and bulbar muscular atrophy; Kennedy disease), Arachidonate 15-lipoxygenase, Arachidonate omega-6 lipoxygenase, BCYM3, BXR, CMT2C, CP2C9_HUMAN, CP33, CP34, CP3A4_HUMAN, CPC9, CYP2C, CYP2C10, CYP3, CYP3A, CYP3A3, CYP3A4, CYPIIC9, CYPIIIA3, CYPIIIA4, Capsaicin receptor, Cytochrome P-450MP, Cytochrome P450 2C9, Cytochrome P450 3A3, Cytochrome P450 3A4, Cytochrome P450 HLp, Cytochrome P450 MP-4, Cytochrome P450 MP-8, Cytochrome P450 NF-25, Cytochrome P450 PB-1, Cytochrome P450 family 3 subfamily A polypeptide 4, Cytochrome P450 subfamily IIIA polypeptide 4, Cytochrome P450, family 2, subfamily C, polypeptide 9, Cytochrome P450-PCN1, DHTR, DKFZp434K0220, DNA binding protein, Dihydro testosterone receptor, Dihydrotestosterone receptor (DHTR), GCCR, GCPS, GCRST, GCR_HUMAN, GLI Kruppel family member GLI 3, GLI Kruppel family member GLI3 (Greig cephalopolysyndactyly syndrome), GLI family zinc finger 3, GLI3 C-terminally truncated form, GLI3 form of 190 kDa, GLI3 form of 83 kDa, GLI3 full length protein, GLI3-190, GLI3-83, GLI3FL, GLI3_HUMAN, GR, Glioma associated oncogene family zinc finger 3, Glucocorticoid inducible P450, Glucocorticoid receptor, Grl1, HLP, HMSN2C, HUMARA, HYSP1, KD, Kennedy disease (KD), LOG15, LOX15_HUMAN, MGC12549, MGC126680, MGC149605, MGC88320, Microsomal monooxygenase, NF 25, NR1I2_HUMAN, NR3C3, NR3C4, Nifedipine oxidase, Nuclear receptor subfamily 1 group I member 2, Nuclear receptor subfamily 3 group C member 1, Nuclear receptor subfamily 3 group C member 3, Nuclear receptor subfamily 3 group C member 4, Nuclear receptor subfamily 3 group C member 4 (NR3C4), ONR 1, OSM9 like transient receptor potential channel 4, OTRPC 4, OTRPC1, OTRPC2, OTTHUMP00000020135, OTTHUMP00000215173, OTTHUMP00000215174, OTTHUMP00000215175, Oncogene GLI3, Orphan nuclear receptor PAR 1, Orphan nuclear receptor PXR, Osm-9-like TRP channel 1, Osm-9-like TRP channel 2, Osm-9-like TRP channel 4, Osmosensitive transient receptor potential channel 4, P450 III steroid inducible, P450 MP, P450 PB 1, P450 PCN1, P450, family III, P450C3, P450IIC9, PAP A, PAPB, PAR, PAR q, PGR, PPD IV, PR, PRA, PRB, PRGR_HUMAN, PRR, Pregnane X receptor, Progesterone receptor, Progestin receptor form A, Progestin receptor form B, Quinine 3-monooxygenase, S-mephenytoin 4-hydroxylase, SBMA, SMAL, SMAX1, SPSMA, SSQTL1, SXR, Sac2b, Spinal and bulbar muscular atrophy, Spinal and bulbar muscular atrophy (SBMA), Steroid and xenobiotic receptor, Stretch activated channel 2B, TFM, TRP 12, TRPV1_HUMAN, TRPV2_HUMAN, TRPV4_HUMAN, Taurochenodeoxycholate 6-alpha-hydroxylase, Testicular Feminization (TFM), Transcriptional activator GLI3, Transcriptional repressor GLI3R, Transient receptor potential cation channel subfamily V member 1, Transient receptor potential cation channel subfamily V member 2, Transient receptor potential cation channel subfamily V member 4, Transient receptor potential protein 12, VR 1, VR 4, VR-OAC, VRL, VRL-1, VRL-2, Vanilloid receptor 1, Vanilloid receptor subtype 1, Vanilloid receptor-like channel 2, Vanilloid receptor-like protein 1, Vanilloid receptor-like protein 2, Vanilloid receptor-related osmotically-activated channel, Xenobiotic monooxygenase, Zinc finger protein GLI 3, androgen receptor splice variant 4b, cytochrome P-450 S-mephenytoin 4-hydroxylase, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 3, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 4, flavoprotein-linked monooxygenase, glucocorticoid nuclear receptor variant 1, nr3c1, nuclear receptor subfamily 3, group C, member 1 (glucocorticoid receptor), pregnane X nuclear receptor variant 2

1 Images
Chemical Structure - Nonivamide, TRPV1 agonist (AB144652)
  • Chemical Structure

Lab

Chemical Structure - Nonivamide, TRPV1 agonist (AB144652)

2D chemical structure image of ab144652, Nonivamide, TRPV1 agonist

Key facts

CAS number

2444-46-4

Purity

>98%

Form

Solid

form

Molecular weight

293.4 Da

Molecular formula

C<sub>1</sub><sub>7</sub>H<sub>2</sub><sub>7</sub>NO<sub>3</sub>

PubChem

2998

Nature

Synthetic

Solubility

Soluble in ethanol to 100 mM

Soluble in DMSO to 100 mM

Biochemical name

Nonivamide

Biological description

TRPV1 agonist. Less potent Capsaicin (ab141000) analog. Induces Ca2+ release from ER. Blood-brain barrier permeable. Active in vivo.

Canonical smiles

CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC

InChi

InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)

InChiKey

RGOVYLWUIBMPGK-UHFFFAOYSA-N

IUPAC Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
+4°C
Appropriate long-term storage conditions
+4°C

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

TRPV1 also known as the capsaicin receptor is a receptor channel with a mass of approximately 95 kDa. This protein is a member of the transient receptor potential vanilloid family and is mainly expressed in sensory neurons such as those found in the dorsal root ganglia. Glucocorticoid Receptor also referred to as NR3C1 is a nuclear receptor with a mass of about 86 kDa expressed broadly in many tissues. The Progesterone Receptor found predominantly in the reproductive tissues has a molecular weight of 98 kDa. TRPV2 is another temperature-sensitive ion channel similar to TRPV1 and is expressed in several tissue types including cardiac muscle. Gli3 serves as a transcription factor in the Hedgehog signaling pathway with mass around 190 kDa and functions mostly in neural tissue. Cytochrome P450 3A4 (CYP3A4) and CYP2C9 enzymes present in the liver play essential roles in drug metabolism. The Androgen Receptor weighing about 110 kDa is important for signaling in male reproductive tissues. PXR or Pregnane X Receptor expressed in the liver and intestine is an important regulator of CYP3A4. TRPV4 another member of the TRPV family functions in osmo- and mechanosensation and is expressed in various tissues like lung and kidney. 15-Lipoxygenase 1 (15-LOX1) is an enzyme involved in the metabolism of polyunsaturated fatty acids.
Biological function summary

Expression and interaction of these proteins participate in various cellular mechanisms. TRPV1 detects heat and pH changes integrating pain and heat sensations while TRPV2 responds to mechanical stimuli possibly interacting in immune cells. The Glucocorticoid Receptor mediates stress responses by regulating gene expression usually forming a receptor-ligand complex. Progesterone and Androgen receptors regulate reproductive system development and function through gene regulation. Gli3 acts in developing tissue particularly influencing organismal growth via transcriptional regulation. Cytochromes CYP3A4 and CYP2C9 metabolize pharmaceuticals and are part of a group of enzymes that facilitate detoxification processes. The PXR receptor supports the transcription of metabolizing genes. It often complexes with CYP3A4 affecting drug clearance rates. TRPV4 influences cellular volume and ion homeostasis while 15-LOX1 contributes to the inflammatory response by oxidizing fatty acids.

Pathways

These proteins form key components in multiple signaling routes. TRPV1 and TRPV4 for instance contribute significantly to the transduction of sensory signaling pathways pertinent to pain and temperature regulation. The Glucocorticoid Receptor plays a part in the stress-adaptive HPA axis pathway linking with various other receptors. CYP3A4 and CYP2C9 are integral to the xenobiotic metabolism pathway where they relate closely to detoxification proteins like PXR. The Androgen Receptor significantly impacts the androgen signaling pathway directly influencing reproductive system development and maintenance. Gli3 occupies a space in the Hedgehog signaling pathway collaborating closely with other transcription factors.

These targets show association with specific pathologies. TRPV1 links to chronic pain conditions and the modulation of its activity may provide relief. Similarly TRPV4 is involved in hereditary neuropathy. Anomalies in the Glucocorticoid Receptor may lead to glucocorticoid resistance while dysregulation of the Progesterone Receptor has associations with reproductive tract cancers. Aberrant functioning of CYP3A4 connected to PXR and Cytochrome P450 systems influences drug interaction disorders. Dysfunction in Androgen Receptors can contribute to conditions such as prostate cancer. Inflammation and respiratory issues can link to altered 15-LOX1 activity. Misregulated Gli3 signaling can result in developmental disorders like Pallister-Hall syndrome.

Product protocols

Product promise

We are committed to supporting your work with high-quality reagents, and we're here for you every step of the way. In the unlikely event that one of our products does not perform as expected, you're protected by our Product Promise.
For full details, please see our Terms & Conditions

Please note: All products are 'FOR RESEARCH USE ONLY. NOT FOR USE IN DIAGNOSTIC OR THERAPEUTIC PROCEDURES'.

For licensing inquiries, please contact partnerships@abcam.com