PRODUCTS

NICOTINAMIDE (NAM)

Nicotinamide (NAM) is a pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.
Nicotinamide (NAM) has a role as an EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor, a metabolite, a cofactor, an antioxidant, a neuroprotective agent, an EC 3.5.1.98 (histone deacetylase) inhibitor, an anti-inflammatory agent, a Sir2 inhibitor, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite, a human urinary metabolite and a geroprotector.
Nicotinamide (NAM) is a vitamin B3, a pyridinecarboxamide and a pyridine alkaloid.
Nicotinamide (NAM) is functionally related to a nicotinic acid.

CAS: 98-92-0
European Community (EC) Number: 202-713-4

IUPAC Name: pyridine-3-carboxamide

Molecular Formula: C6H6N2O
Molecular Weight: 122.12 g/mol

Niacinamide or nicotinamide is a form of vitamin B3 found in food and used as a dietary supplement and medication.
As a supplement, Nicotinamide (NAM) is used by mouth to prevent and treat pellagra (niacin deficiency).
While nicotinic acid (niacin) may be used for this purpose, niacinamide has the benefit of not causing skin flushing.
As a cream, Nicotinamide (NAM) is used to treat acne.
Nicotinamide (NAM) is a water-soluble vitamin.
Niacinamide is the supplement name while nicotinamide is the scientific name.

Normal amounts are safe for use during pregnancy.
Nicotinamide (NAM) is in the vitamin B family of medications, specifically the vitamin B3 complex.
Nicotinamide (NAM) is an amide of nicotinic acid.
Foods that contain Nicotinamide (NAM) include yeast, meat, milk, and green vegetables.

Nicotinamide (NAM) was discovered between 1935 and 1937.
Nicotinamide (NAM) is on the World Health Organization's List of Essential Medicines.
Nicotinamide (NAM) is available as a generic medication and over the counter.
Commercially, Nicotinamide (NAM) is made from either nicotinic acid (niacin) or nicotinonitrile.
In some countries grains have Nicotinamide (NAM) added to them.

Nicotinamide (NAM) is the amide form of vitamin B3 (niacin).
Severe vitamin B3 deficiency causes pellagra, a systemic disease exhibiting the signature ‘‘4 Ds’’: diarrhea, dermatitis, dementia, and, ultimately, death.
Using NAM as a dietary supplement to prevent and treat pellagra was a monumental public health advance.

Nicotinamide (NAM), nicotinic acid and nicotinamide riboside are vitamin B3 precursors of NAD+ in the human diet.
NAD+ has a fundamental importance for cellular biology, that derives from its essential role as a cofactor of various metabolic redox reactions, as well as an obligate co-substrate for NAD+-consuming enzymes which are involved in many fundamental cellular processes including aging/longevity.
During aging, a systemic decrease in NAD+ levels takes place, exposing the organism to the risk of a progressive inefficiency of those processes in which NAD+ is required and, consequently, contributing to the age-associated physiological/functional decline.

Nicotinamide (NAM) is a cell culture supplement used in the differentiation of embryonic stem (ES) and induced pluripotent stem (iPS) cells.
Nicotinamide (NAM) is an amide derivative of vitamin B3, a poly (ADP-ribose) polymerase (PARP) inhibitor, and represents the primary precursor of NAD+.
Nicotinamide has also been shown to modulate stem cell differentiation in various applications, most notably for the differentiation of pancreatic mouse ES and iPS cells to pancreatic islet-like insulin-secreting cells.

An important compound functioning as a component of the coenzyme NAD.
Nicotinamide (NAM)s primary significance is in the prevention and/or cure of blacktongue and pellagra.
Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake.

Medical uses

Niacin deficiency
Nicotinamide (NAM) is the preferred treatment for pellagra, caused by niacin deficiency.

Acne
Nicotinamide (NAM) cream is used as a treatment for acne.
Nicotinamide (NAM) has anti-inflammatory actions, which may benefit people with inflammatory skin conditions.

Nicotinamide (NAM) increases the biosynthesis of ceramides in human keratinocytes in vitro and improves the epidermal permeability barrier in vivo.
The application of 2% topical Nicotinamide (NAM) for 2 and 4 weeks has been found to be effective in lowering the sebum excretion rate.
Nicotinamide (NAM) has been shown to prevent Cutibacterium acnes-induced activation of toll-like receptor 2, which ultimately results in the down-regulation of pro-inflammatory interleukin-8 production.

Skin cancer
Nicotinamide (NAM) at doses of 500 to 1000 mg a day decreases the risk of skin cancers, other than melanoma, in those at high risk.

Chemistry
The structure of nicotinamide consists of a pyridine ring to which a primary amide group is attached in the meta position.
Nicotinamide (NAM) is an amide of nicotinic acid.
As an aromatic compound, Nicotinamide (NAM) undergoes electrophilic substitution reactions and transformations of its two functional groups.
Examples of these reactions reported in Organic Syntheses include the preparation of 2-chloronicotinonitrile by a two-step process via the N-oxide, from nicotinonitrile by reaction with phosphorus pentoxide, and from 3-aminopyridine by reaction with a solution of sodium hypobromite, prepared in situ from bromine and sodium hydroxide.

Industrial production
The hydrolysis of nicotinonitrile is catalysed by the enzyme nitrile hydratase from Rhodococcus rhodochrous J1, producing 3500 tons per annum of nicotinamide for use in animal feed.
The enzyme allows for a more selective synthesis as further hydrolysis of the amide to nicotinic acid is avoided.
Nicotinamide can also be made from nicotinic acid.

Biochemistry

Nicotinamide, as a part of the cofactor nicotinamide adenine dinucleotide (NADH / NAD+) is crucial to life.
In cells, nicotinamide is incorporated into NAD+ and nicotinamide adenine dinucleotide phosphate (NADP+).
NAD+ and NADP+ are cofactors in a wide variety of enzymatic oxidation-reduction reactions, most notably glycolysis, the citric acid cycle, and the electron transport chain.
If humans ingest nicotinamide, it will likely undergo a series of reactions that transform it into NAD, which can then undergo a transformation to form NADP+.
This method of creation of NAD+ is called a salvage pathway.
However, the human body can produce NAD+ from the amino acid tryptophan and niacin without our ingestion of nicotinamide.

NAD+ acts as an electron carrier that mediates the interconversion of energy between nutrients and the cell's energy currency, adenosine triphosphate (ATP).
In oxidation-reduction reactions, the active part of the cofactor is the nicotinamide.
In NAD+, the nitrogen in the aromatic nicotinamide ring is covalently bonded to adenine dinucleotide.
The formal charge on the nitrogen is stabilized by the shared electrons of the other carbon atoms in the aromatic ring.
When a hydride atom is added onto NAD+ to form NADH, the molecule loses its aromaticity, and therefore a good amount of stability.
This higher energy product later releases its energy with the release of a hydride, and in the case of the electron transport chain, it assists in forming adenosine triphosphate.

When one mole of NADH is oxidized, 158.2 kJ of energy will be released.

Biological role
Nicotinamide occurs as a component of a variety of biological systems, including within the vitamin B family and specifically the vitamin B3 complex.
Nicotinamide (NAM) is also a critically important part of the structures of NADH and NAD+, where the N-substituted aromatic ring in the oxidised NAD+ form undergoes reduction with hydride attack to form NADH.
The NADPH/NADP+ structures have the same ring, and are involved in similar biochemical reactions.

Nicotinamide can be methylated in the liver to biologically active 1-Methylnicotinamide when there's sufficient methyl donors.

Food sources
Nicotinamide (NAM) occurs in trace amounts mainly in meat, fish, nuts, and mushrooms, as well as to a lesser extent in some vegetables.
Nicotinamide (NAM) is commonly added to cereals and other foods.
Many multivitamins contain 20–30 mg of vitamin B3 and it is also available in higher doses.

Experimental Properties

Physical Description: Nicotinamide is a white powder.
Color / Form: White, powder, needles from benzene
Odor: Odorless
Taste: Bitter taste
Boiling Point: 302 to 320 °F at 760 mmHg
Melting Point: 264 to 268 °F
Flash Point: 182 °C
Solubility: 2.8 [ug/mL] (The mean of the results at pH 7.4)
Density: 1.4
Vapor Density: Relative vapor density (air = 1): 4.2
Vapor Pressure: 4.2X10-4 mm Hg at 25 °C (est)
Autoignition Temperature :480 °C
pH: 10% "wt in vol" solution in water is neutral to litmus

SYNONYMS:

nicotinamide
niacinamide
98-92-0
3-Pyridinecarboxamide
Nicotinic acid amide
pyridine-3-carboxamide
vitamin PP
Papulex
Aminicotin
Amixicotyn
Nicobion
Nicotylamide
Nikotinamid
Savacotyl
Benicot
Dipegyl
Endobion
Hansamid
Pelmine
Nicotinic amide
Delonin amide
Pelonin amide
Vi-Nicotyl
Austrovit PP
Inovitan PP
Nicosylamide
Nicotilamide
Nicotililamido
Amnicotin
Niacevit
Nicamina
Nicamindon
Nicofort
Nicomidol
Nicotamide
Nicovitina
Nicovitol
Nicozymin
Niocinamide
Niozymin
Niamide
Nicasir
Nicogen
Nicota
Nicotol
Nicovit
Niko-tamin
3-Carbamoylpyridine
Nicotine acid amide
Nandervit-N
Pyridine-3-carboxylic acid amide
Vitamin B
Niavit PP
Nicotinamidum
Nicosan 2
Nicotine amide
beta-Pyridinecarboxamide
Nikotinsaeureamid
Nicotylamidum
Mediatric
Nicotinsaureamid
Pyridine, 3-carbamoyl-
3-Pyridinecarboxylic acid amide
m-(Aminocarbonyl)pyridine
Acid amide
Factor pp
Nicotinamida
Nicovel
Vitamin B (VAN)
Pelmin
Amid kyseliny nikotinove
Witamina PP
PP-Faktor
Amide PP
Nicotinsaureamid [German]
Nikotinsaeureamid [German]
Amid kyseliny nikotinove [Czech]
Nicotinamidum [INN-Latin]
Nicotinamida [INN-Spanish]
NAM
Niacinamide [USAN]
C6H6N2O
Niacinamid
Nictoamide
CCRIS 1901
Dipigyl
HSDB 1237
Vi-noctyl
3-(aminocarbonyl)pyridine
AI3-02906
NSC 13128
b-Pyridinecarboxamide
Niacinamide [USP]
Nicotinamide [INN]
EINECS 202-713-4
MFCD00006395
NSC-13128
NSC-27452
.beta.-Pyridinecarboxamide
Nicotinamide-(amide-15N)
Nicotinamide (Vitamin B3)
CHEMBL1140
UNII-25X51I8RD4
MLS000069714
DEA No. 1405
DTXSID2020929
CHEBI:17154
25X51I8RD4
NSC13128
Niacinamide (USP)
NCGC00093354-03
NCGC00093354-05
SMR000058212
Nicotinamide 10 microg/mL in Acetonitrile
Niacinamide;Nicotinic acid amide;Vitamin B3
WLN: T6NJ CVZ
EC 202-713-4
DTXCID00929
CAS-98-92-0
SR-01000721872
nicotin-amide
3-Amidopyridine
Nicotinamide,(S)
Vitamin B3 amide
3-yridinecarboxamide
3-piridinacarboxamida
Mediatric (Salt/Mix)
niacin - Vitamin B3
1yc5
Opera_ID_775
Niacin (as niacinamide)
NIACINAMIDE [II]
Niacinamide(Vitamin B3)
NIACINAMIDE [FCC]
NICOTINAMIDE [MI]
Niacinamide (nicotinamide)
NIACINAMIDE [HSDB]
NIACINAMIDE [INCI]
NICOTINAMIDE [JAN]
bmse000281
MolMap_000061
NIACINAMIDE [VANDF]
SCHEMBL2926
Nicotinamide (JP17/INN)
NICOTINAMIDUM [HPUS]
NIACINAMIDE [USP-RS]
NICOTINAMIDE [MART.]
MLS001424246
NICOTINAMIDE [WHO-DD]
NICOTINAMIDE [WHO-IP]
SCHEMBL6278767
SGCUT00176
TPN COMPONENT NIACINAMIDE
SCHEMBL19978192
BDBM27507
NIACINAMIDE [ORANGE BOOK]
HMS2052M21
HMS2090B05
HMS2093H03
HMS2236J03
HMS3370F21
HMS3394M21
HMS3655M20
HMS3713B22
HMS3884A16
NICOTINAMIDE [EP IMPURITY]
Pharmakon1600-01505397
NIACINAMIDE [USP MONOGRAPH]
NICOTINAMIDE [EP MONOGRAPH]
BCP07322
HY-B0150
NIACINAMIDE COMPONENT OF TPN
NSC27452
to_000073
EINECS 234-265-0
Nicotinamide 1.0 mg/ml in Methanol
Nicotinamide, >=98.5% (HPLC)
Nicotinamide, >=99.5% (HPLC)
Tox21_111202
Tox21_201716
Tox21_302776
NICOTINAMIDUM [WHO-IP LATIN]
NSC759115
s1899
STL163867
AKOS005715850
Tox21_111202_1
CCG-101149
CS-1968
CS-O-30679
DB02701
LS-2051
NC00399
NSC-759115
SB74497
Nicotinamide 100 microg/mL in Methanol
Nicotinamide, >=98% (HPLC), powder
NCGC00093354-04
NCGC00093354-06
NCGC00093354-09
NCGC00256432-01
NCGC00259265-01
NIACIN (AS NIACINAMIDE) [VANDF]
11032-50-1
AS-13845
BN166252
Nicotinamide, puriss., 99.0-101.0%
SY024804
Nicotinamide, tested according to Ph.Eur.
SBI-0206826.P001
FT-0631517
FT-0672696
FT-0773644
N0078
SW197779-3
EN300-15612
Niacinamide, meets USP testing specifications
C00153
D00036
Nicotinamide (Niacinamide), analytical standard
AB00373895-13
AB00373895_15
AB00373895_16
Nicotinamide, Vetec(TM) reagent grade, >=98%
A845925
AC-907/25014114
Q192423
Q-201470
SR-01000721872-3
SR-01000721872-4
SR-01000721872-5
Z33546463
F2173-0513
Niacinamide;Nicotinic acid amide;Vitamin B3; Vitamin PP
Nicotinamide, British Pharmacopoeia (BP) Reference Standard
A186B02E-6C70-4E54-9739-79398D439AAA
Nicotinamide, European Pharmacopoeia (EP) Reference Standard
Niacinamide, United States Pharmacopeia (USP) Reference Standard
InChI=1/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9
Niacinamide, Pharmaceutical Secondary Standard; Certified Reference Material
Nicotinamide, BioReagent, suitable for cell culture, suitable for insect cell culture