(Rac)-Indoximod (1-Methyl-DL-tryptophan) is an indoleamine-2,3-dioxygenase (IDO) inhibitor. The combination of (Rac)-Indoximod and IFN-γ significantly reduced the activity of human cardiac fibroblasts expressing α-SMA and induced apoptosis by up-regulating IRF-1, Fas and FasL genes.

Physicochemical Properties

Molecular Formula	C12H14N2O2
Molecular Weight	218.25
Exact Mass	218.106
CAS #	26988-72-7
Related CAS #	Indoximod;110117-83-4;(S)-Indoximod;21339-55-9
PubChem CID	98112
Appearance	White to off-white solid powder
Density	1.28g/cm3
Boiling Point	429.3ºC at 760mmHg
Melting Point	250ºC (dec.)(lit.)
Flash Point	213.4ºC
LogP	1.833
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Heavy Atom Count	16
Complexity	270
Defined Atom Stereocenter Count	0
InChi Key	ZADWXFSZEAPBJS-UHFFFAOYSA-N
InChi Code	InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)
Chemical Name	2-amino-3-(1-methylindol-3-yl)propanoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	IDO
ln Vitro	(Rac)-Indoximod (1-methyl-DL-tryptophan; 0.5 mM; 3 days) prevents tryptophan depletion independent of tryptophan depletion, but it also inhibits tryptophan elimination, partially reversing the growth inhibitory action of IFN-γ. may cause cellular death [1].
Cell Assay	Cell Viability Assay[1] Cell Types: Human cardiac myofibroblasts (hCMs) Tested Concentrations: 0.5 mM Incubation Duration: 3 days Experimental Results: Growth retardation by IFN-γ was partially reversed on day 2, but cell viability was further decreased on day 3.
References	[1]. Co-treatment with interferon-γ and 1-methyl tryptophan ameliorates cardiac fibrosis through cardiac myofibroblasts apoptosis. Mol Cell Biochem. 2019 Aug;458(1-2):197-205.
Additional Infomation	1-methyltryptophan is a tryptophan derivative that is tryptophan carrying a single methyl substituent at position 1 on the indole. It has a role as an EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor and an antineoplastic agent. It is a non-proteinogenic alpha-amino acid and a tryptophan derivative. 1-Methyl-DL-tryptophan has been reported in Aspergillus fumigatus with data available. See also: 1-methyl-L-tryptophan (annotation moved to).

Solubility Data

Solubility (In Vitro)

0.1 M NaOH : 10 mg/mL (45.82 mM) DMSO : 4.76 mg/mL (21.81 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.5819 mL	22.9095 mL	45.8190 mL
	5 mM	0.9164 mL	4.5819 mL	9.1638 mL
	10 mM	0.4582 mL	2.2910 mL	4.5819 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.