ChemicalBook > CAS DataBase List > 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one

2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one

Product Name
2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one
CAS No.
5291-32-7
Chemical Name
2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one
Synonyms
PRIMA-1MET;APR-246;Eprenetapopt;APR246;APR 246;PRIMA-1MET(APR-246);APR-246 (PRIMA-1MET);Eprenetapopt (APR246;PRIMA-1MET;PRIMA-1MET, p53 activity;Eprenetapopt, 10 mM in DMSO
CBNumber
CB52518928
Molecular Formula
C10H17NO3
Formula Weight
199.25
MOL File
5291-32-7.mol
More
Less

2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Property

Melting point:
115-116 °C
Boiling point:
313.8±17.0 °C(Predicted)
Density 
1.20±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
Soluble in DMSO (up to 20 mg/ml)
form 
powder
pka
13.99±0.10(Predicted)
color 
white to beige
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChI
1S/C10H17NO3/c1-14-7-10(6-12)9(13)8-2-4-11(10)5-3-8/h8,12H,2-7H2,1H3
InChIKey
BGBNULCRKBVAKL-UHFFFAOYSA-N
SMILES
N21CCC(CC2)C(=O)C1(COC)CO
More
Less

Safety

WGK Germany 
WGK 3
Storage Class
11 - Combustible Solids
Hazard Classifications
Eye Irrit. 2
Skin Irrit. 2
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML1789
Product name
PRIMA-1Met
Purity
≥98% (HPLC)
Packaging
5mg
Price
$125
Updated
2026/03/19
Sigma-Aldrich
Product number
SML1789
Product name
PRIMA-1Met
Purity
≥98% (HPLC)
Packaging
25mg
Price
$511
Updated
2026/03/19
TCI Chemical
Product number
E1608
Product name
PRIMA-1MET
Purity
min. 95.0 %
Packaging
5MG
Price
$71
Updated
2026/03/19
TCI Chemical
Product number
E1608
Product name
PRIMA-1MET
Purity
min. 95.0 %
Packaging
25MG
Price
$229
Updated
2026/03/19
Cayman Chemical
Product number
9000487
Product name
PRIMA-1MET
Purity
≥95%
Packaging
5mg
Price
$68
Updated
2024/03/01
More
Less

2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Chemical Properties,Usage,Production

Description

PRIMA-1MET(5291-32-7) reactivates mutant p53, an important tumor suppressor gene, in cancer cells.1It induces p53-dependent mitochondrial apoptosisviaactivation of caspase-2.2PRIMA-1METshowed significant antitumor activity in multiple myelomaviaactivation of p733and had previously been shown to target p53 family members p63 and p734. Tumor cell death by PRIMA-1METhas been also shown to be caused by glutathione depletion and induced ROS production in a p53 independent manner.5-7PRIMA-1METprobably induces tumor cell death by both reactivating mutant p53 and inhibiting cellular thiol-dependent redox systems.8

Uses

2-(Hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one is a small molecule that has shown promising preclinical activity in various cancer types. 2-(Hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one shows antitumor activity in multiple myeloma by induction of p73 and Noxa.

Biochem/physiol Actions

PRIMA-1Met, also called APR-246, is converted to methylene quinuclidinone (MQ), a Michael acceptor. It interacts with p53 through the cysteine (Cys) residue. It blocks the thioredoxin reductase (TrxR1) enzyme. It is under clinical investigation and well-studied. PRIMA-1Met effect is tested on breast cancer specific gene expression.

storage

Store at +4°C

References

[1] VLADIMIR J N BYKOV. PRIMA-1MET synergizes with cisplatin to induce tumor cell apoptosis[J]. Oncogene, 2005, 24 21: 3484-3491. DOI:10.1038/sj.onc.1208419
[2] J SHEN. PRIMA-1MET induces mitochondrial apoptosis through activation of caspase-2[J]. Oncogene, 2008, 27 51: 6571-6580. DOI:10.1038/onc.2008.249
[3] MANUJENDRA N SAHA. PRIMA-1Met/APR-246 displays high antitumor activity in multiple myeloma by induction of p73 and Noxa.[J]. Molecular Cancer Therapeutics, 2013: 2331-2341. DOI:10.1158/1535-7163.mct-12-1166
[4] N RÖKAEUS. PRIMA-1MET/APR-246 targets mutant forms of p53 family members p63 and p73[J]. Oncogene, 2010, 29 49: 6442-6451. DOI:10.1038/onc.2010.382
[5] BENOÎT TESSOULIN. PRIMA-1Met induces myeloma cell death independent of p53 by impairing the GSH/ROS balance.[J]. Blood, 2014, 124 10: 1626-1636. DOI:10.1182/blood-2014-01-548800
[6] DAVID S LIU. Inhibiting the system xC-/glutathione axis selectively targets cancers with mutant-p53 accumulation.[J]. Nature Communications, 2017: 14844. DOI:10.1038/ncomms14844
[7] NAOISE C. SYNNOTT . The Mutant p53-Targeting Compound APR-246 Induces ROS-Modulating Genes in Breast Cancer Cells[J]. Translational Oncology, 2018, 11 6: Pages 1343-1349. DOI:10.1016/j.tranon.2018.08.009
[8] LENA HAFFO. Inhibition of the glutaredoxin and thioredoxin systems and ribonucleotide reductase by mutant p53-targeting compound APR-246.[J]. Scientific Reports, 2018: 12671. DOI:10.1038/s41598-018-31048-7

2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Suppliers

China 118 India 1 United Kingdom 1 United States 14 Global 134
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15838
Advantage
69
VDM Biochemicals
Tel
0330-2528181
Fax
0330-2528171
Email
sales@vdmbio.com
Country
United States
ProdList
510
Advantage
64
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
12952
Advantage
65
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
sales@meilune.com
Country
China
ProdList
4790
Advantage
58
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
AdooQ BioScience, LLC
Tel
+1 (866) 930-6790
Fax
+1 (866) 333-9607
Email
info@adooq.com
Country
United States
ProdList
2782
Advantage
58
ShangHai Caerulum Pharma Discovery Co., Ltd.
Tel
18149758185 18149758185
Email
sales-cpd@caerulumpharma.com
Country
China
ProdList
3505
Advantage
58
Shanghai Balmxy Pharmaceutical Co., Ltd
Tel
021-24206007 13764915196
Fax
86-021-23027023
Email
sales@balmxy.com
Country
China
ProdList
6921
Advantage
55
Shanghai Tombiopharma Chemical Co. Ltd.
Tel
13391076197
Email
tombiopharma@163.com
Country
China
ProdList
4987
Advantage
55
AdooQ Bioscience CHINA
Tel
025-58849295 18951903616;
Fax
025-68650336
Email
info@adooq.cn
Country
China
ProdList
2990
Advantage
60
More
Less

View Lastest Price from 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
APR-246 (PRIMA-1MET) 5291-32-7
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
Hubei XinRunde Chemical Co., Ltd.
Product
APR-246 (PRIMA-1MET) 5291-32-7
Price
US $10.00/KG
Min. Order
10KG
Purity
99
Supply Ability
10MT
Release date
2018-06-19

5291-32-7, 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-oneRelated Search:

Imatinib mesylate LFM-A13 AG 490 (+)-Camptothecin

  • 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one
  • PRIMA-1MET
  • APR-246
  • PRIMA-1<sup>MET</sup>
  • APR-246 (PRIMA-1MET)
  • PRIMA-1MET(APR-246)
  • APR246;APR 246
  • PRIMA-1MET 2-(Hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one APR-246
  • 2-(Hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one
  • 1-Azabicyclo[2.2.2]octan-3-one, 2-(hydroxymethyl)-2-(methoxymethyl)-
  • 2-(Hydroxymethyl)-2-(methoxymethyl)-3-quinuclidinone
  • Eprenetapopt
  • Eprenetapopt (APR246
  • PRIMA-1MET, p53 activity
  • Eprenetapopt, 10 mM in DMSO
  • Eprenetapopt (APR-246) ，S7724
  • 5291-32-7